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Editor’s notes: These are Bobby’s picks - not staff selections. They are in no way predictable; you might even call them eclectic, but I like that. They are in alphabetical order, not ranked. I added a few links in the song titles, particularly a few more obscure choices, and there are a few videos scattered throughout. This is part 2. Here’s part 1 if you missed it. ~Trailer
By Bobby Peacock
Steve's probably going to hate me for this one... Long before his brief radio success with "I Don't Have to Be Me ('til Monday)," I owned a copy of this album and enjoyed it. While not as bluesy as his later efforts, it's no less compelling and gritty. You think the relationship is in peril from one big fight, until he points out that it's okay; there's too much at stake for me to just give up. It's an uncommon twist with a charismatic vocal. Maybe there's that extra bit of joy from being able to say "I knew him before he was famous" every time I hear "Monday," but I think this song has enough merit to stand on its own.
102. "I Was" by Neal McCoy (#37, 1999)
The narrator picks up a female hitchhiker who strikes up a conversation, where both of them realize that they're trying to escape from situations that they're not happy with. He's just had his heart broken and just wants to clear his head; she's cut ties with college and her boyfriend after being dissatisfied with both. It's an incredibly charming character sketch (one of the best of when Phil Vassar still knew how to write such songs), and probably the best match for Neal at his most charismatic. If he'd found more songs of this ilk sooner, then he might not have been pigeonholed as a novelty act.
I told you the sentence "I would watch the Detroit Tigers on the radio" wasn't a typo. I'm one of the last generations to have grown up with the radio playing a key influence in my life. Obviously that shows in this list, but also in my fond memories of hearing baseball game play-by-plays, church services, Paul Harvey's The Rest of the Story, and so on. While my experiences aren't quite the same as Lionel's here, the underlying theme is so packed with positive memories that I watch this song every time it comes on the radio.
104. "I Wonder How Far It Is Over You" by Aaron Tippin (#40, 1991)
This man is so brought down by his lost love that he ditches his car and just... walks. Turns out he's made quite some distance, but she's still on his mind. It might be hard to believe that someone has made it all the way from Texas to California on foot, but does he ever sell it. Just listen to the way he bends his voice on the phrase "I thought we were through," and how nicely the fiddle complements his completely distraught phrasing. With the momentum of his first single, how did this one not take off too?
105. "I'd Be Better Off (In a Pine Box)" by Doug Stone (#4, 1990)
She's left him for another man and he's so far down in the dumps that he would rather be dead (possibly indicating a plan to commit suicide?) or imprisoned than to bear another moment knowing that she's with someone else. Silly him, thinking that she just wanted her space for a while! Doug Stone has the perfectly reedy, emotive, tearful voice to latch onto this extremely sad lyric, showing his artistic strengths right out of the gate. Yet another example of the kind of artistic risks that an entire career can be built on.
106. "I'd Rather Ride Around with You" by Reba McEntire (#2, 1997)
I've always loved this one's carefree theme of ditching a best friend's wedding to ride around with a friend. Because weddings are just a big pile of decisions and she's not ready for that. Every time I hear this song, I just picture the contrast between the emotion-wrought new bride and the devil-may-care attitude of the narrator, who's probably doing 80 in her Miata down some old country road (something I could see Tuca from Tuca & Bertie doing if Bertie ever got married). Sometimes even lighthearted fare manages to be compelling in unexpected ways.
107. "If I Never Stop Loving You" by David Kersh (#3, 1997-98)
There are lots of ways to express love, but leave it to Skip Ewing to pen a take I don't think I've ever heard before: circumlocution. This guy is so flustered that he's literally talking all around what he's trying to say, adding way more words than necessary (something I'm way too guilty of) and stacking up way too many double-negatives in his attempts to ask for his girl's hand in marriage. (I especially love the line "I mean everything I think I just said".) And Kersh has the youthful charm to pull it off in spades.
108. "If You Ever Have Forever in Mind" by Vince Gill (#5, 1998)
Like most of his strongest cuts, the lyrics say a lot without using a lot of words (a skill I wish I could master for some of these reviews): he wants a long-term relationship, she doesn't, but he's still open if she ever changes her mind. But what really ascends the song to late-90s greatness is the absolutely beautiful countrypolitan-flavored production: a big string section, wall of backing vocals, and piano (Hargus "Pig" Robbins clearly listened to a lot of Floyd Cramer before playing on this song) were the right choice.
Freshly separated from his role as lead singer of Restless Heart, Larry Stewart sets his sights a little more mainstream and hits his target. "Alright Already" was a rock solid start, but this is an even better take on possibly the same heartbreak. His voice pairs well with steel guitar and a brisk shuffle to convey an unusual take: he's "too busy living tonight" to concern himself with the heartbreak that he clearly still has. Sometimes it's better to give yourself room to breathe before concerning yourself with heavy emotion -- so maybe he'll end up recharged and more able to tackle things tomorrow.
110. "I'll Go On Loving You" by Alan Jackson (#3, 1998)
An extremely lush, almost haunting production and a rare '90s use of pure narrative. It's a much darker tone than Alan usually got to try, but he more than pulls it off in a way that foreshadows Like Red on a Rose. There's an unusual sense of sexual energy, tempered by the observation that it's far from the only thing that he wants out of the relationship. Both for the artist and in general, it's an extremely different, ear-catching pledge to everlasting love -- and it seems all the more sincere as a recovery from their widely-publicized separation and marriage counseling.
111. "I'm Gonna Be Somebody" by Travis Tritt (#2, 1990)
The path to the top is not easy, especially for musicians, but there is always a place for hard work and dedication to pay off. And even better yet is when your hard work pays off so thoroughly that it ignites passion in someone else. I don't think I have the dedication to be a full time musician (even though I share a name with this song's protagonist), but every time I hear this song, I hope that whatever I do in life -- even if it's just gushing about '90s country -- will inspire someone. You bet your bottom dollar I will.
112. "I'm in a Hurry (And Don't Know Why)" by Alabama (#1, 1992)
You might not expect me to rank such a lighthearted number so highly ("really, Bobby? This over 'In Pictures'?"), but the truth is, I relate to this song. I constantly find myself rushing at work, rushing at leisure, and even rushing to write this list just so I can do more rushing on the 28,379 other things I want to get done because I have no attention span and feel like I'm way behind my peers. The production and even melody have so much urgency that the song hits its third chorus before two minutes, making this another entry in "songs that sound like the thing they're about".
113. "I'm So Happy I Can't Stop Crying" by Toby Keith featuring Sting (#2, 1997)
A divorced father, unhappy about separation from his kids, clears his head with a nighttime walk and finds himself happier the next day. This resolution turns the song's title from ironic to sincere, and is aided by unconventional song structure. Already great in solo form, it was enhanced as a duet; by merit of completely unpretentious singing and careful selection of which lines are sung by Sting, it seems to become a tale of two men supporting each other after realizing they're both in the same situation. And sometimes, that level of relatability can make a negative situation more bearable.
114. "In a Different Light" by Doug Stone (#1, 1991)
In what almost seems like an antithesis to Linda Davis' "Company Time," the male narrator describes a romantic encounter with an office coworker. She has a conservative, buttoned-down manner to her, but he's the only one who's seen her outside of her business suit with her hair down. The whole time, his reaction to her remains extremely tactful, not letting on the intimate details to anyone else in the song. The markedly urban setting and respect toward women show the kind of growth occurring in Nashville in the '90s -- and Doug Stone's ability to thrive outside his typical heartbreak themes.
115. "In a Heartbeat" by Rodney Atkins (#74, 1997)
A young and very unrecognizable Rodney Atkins -- yes, the same guy who gave us "If You're Going Through Hell (Before the Devil Even Knows)" -- tries on a slightly off-center promise of undying love. A bigger vocal than his later efforts, a high emphasis on guitar, and even a key change in the chorus join a damn strong hook (I also like how the ideas of eyes like stars and wishing on a star are combined into one line) for a surprisingly compelling, Roy Orbison-flavored debut single. Even if this is not what Rodney wanted to be artistically, I still think that he crushed it anyway.
After a lifetime of caring for each other, this elderly farming couple's relationship is nearing its end: the farm's gone, and soon, he will be too. But his deathbed promise to her is that, in his "next life," he'll come back as a better person who can make up for all of his shortcomings. And it's not until the end that you start to realize -- what shortcomings? Clearly these two have loved and supported each other literally all the way to the end, so if any sort of "next life" exists at all, how could it possibly be any better than the one he's already had? Sometimes bittersweetness can be subtle at the same time.
117. "Is It Raining at Your House" by Vern Gosdin (#10, 1990-91)
The Voice is not going unheard on my watch. His last major hit is yet another song that uses very few words to tell a vividly complete story. He's calling her up to talk about the weather -- but is it metaphorical or literal thunder and lightning? Or both? Did he actually get through to her, or is he just leaving a message? Every time I heard this song, I had one last question: does he still love her? And sure enough, Vern answered me at the very last line -- in that tender, heartbroken voice of his, of course.
118. "Is There Life Out There" by Reba McEntire (#1, 1992)
For My Broken Heart is such a strong album that it gets two slots here. This young woman has made choices that aren't sitting right with her, and may or may not be poised to take action. Instead, we're entirely in medias res, watching her mull over the past and angst over the future. By not resolving its conflict -- something that Eddy Raven's "Who Do You Know in California" made me realized is one of my favorite tropes -- the feelings of uncertainty hit all the harder for me, the ever unsure-of-himself writer of this entry.
119. "It Ain't Nothin'" by Keith Whitley (#1, 1990)
Keith Whitley easily could have held his own in the '90s if not for his tragic death from alcohol poisoning. Take for instance this incredibly charmingly tale of mutual support in a relationship. He's having a bad day at work, she's having a bad day at home, but when they're together, all those troubles fade away. It's that sense of reciprocation that gives more depth to the proceedings, and quirky lyrics like "deeper than a well-digger's shoes" and "even Cinderella got to go to the ball" add levity without distracting.
120. "It Must Be Love" by Ty Herndon (#1, 1998)
What are these strange feelings that are making me miss my exit? Clearly it's love that must be keeping me from thinking straight. It's such a common trope, but it's done to perfection here by merit of the clean production, Ty Herndon's ever-on point vocals... and best of all, the back-and-forth chorus. An uncredited Sons of the Desert pose questions ("Is she there in your dreams?"), Ty answers ("I don't know, I can't sleep"), and they both conclude on the title. Above all else, I think it's that extremely uncommon chorus structure alone that propels this one to greatness.
Diamond Rio's ballsiest release. The narrator's mom died in childbirth, and his father is a crazed, conspiratorial sidewalk preacher who dies while snake-handling. It's a very uncommon set of characters, and there's an implication that the narrator is himself a little off-kilter from all of this. All of this builds to a conclusion that certain facts of life are up to interpretation (possibly including the premise of this song). It's that mix of detail and ambiguity -- combined with experimental production and an almost country-rap approach to vocals -- that make this quirky song pay off in spades.
How much harder can a breakup song hit than by writing it with the guy you're about to break up from? I don't know if they were planning to at the time, but it certainly makes the song that much stronger as a taunt toward your soon-to-be-ex. There's a palpable bitterness in lines like "Go on, walk away, but don't say I didn't warn you" and "our love is dying for you to know". Her voice completely sells each barbed line, and the moody production (a surprisingly common thread on this album) more than holds things together.
123. "It's Not Over" by Mark Chesnutt feat. Alison Krauss and Vince Gill (#34, 1997-98)
A beautiful little waltz with a straightforward lyric about heartbreak, and a testament to Mark Wright's underratedness as both songwriter and producer. By keeping things subtle all around, the sound is timeless and beautiful -- two descriptors helped by the addition of Alison Krauss and Vince Gill on backing vocals. At times it's just best to take a concept back to the basics, and this one does it exceptionally well thanks in no small part to that great hook. It's easy to see why Mark saw fit to give this one a second chance.
124. "It's Not the End of the World" by Emilio (#27, 1995)
Unlike The Mavericks, Tejano star Emilio Navaira didn't add many of his Latin influences to his country music (other than a direct Spanish translation titled "No es el fin del mundo"). However, what he did bring was every bit as much passion and energy to an unusual midpoint in typical heartbreak tropes. He knows he's going to get better even if he doesn't feel it yet, and the solace of everyday life is enough to keep him smiling through the pain. It's a very believable take on resilience, and between his voice and the lush production, it sounds beautiful in both English and Spanish.
125. "I've Come to Expect It from You" by George Strait (#1, 1990-91)
He's clearly been maligned in this relationship, as the extremely incisive line "I wouldn't treat a dog the way you treated me / But that's what I get; I've come to expect it from you" makes clear. But after channeling his anger, he turns the title around with one last parting shot: "You'll come back this time to find out that I'm gone / But that's what you get; you should expect that from me." It's extremely different for King George by merit of how angry and bitter it is, but that just makes it all the more of a standout.
The only thing that Shane Sutton did after some songs for the ill-fated Jetsons: The Movie in 1990 was a brief fling on the even more ill-fated Polydor Records. The ex is back in town, and he's well aware of it. The guitar work is spot-on here, and I just always loved the hook: "I've got your number, and honey, that's the reason I don't call." By standing his ground and not giving in to her advances, he sounds wise beyond his years (if the birthdate I found online is correct, he was only 19 when he cut this) -- a feat that few teenage singers, especially country ones, have been able to pull off.
Sometimes childhood friends end up making wrong decisions that drive each other away. In this case, Jenny fell in love with a football player and dropped out to follow him, only for him to dump her and leave her stranded. The narrator doesn't figure out what happened to Jenny until near the end, when it's revealed that she's now working a dead-end job at a movie theater and harboring resentment. Helen's vocal is full of nuance -- twangy, husky, sweet, even talk-singing at times -- sounds like almost no one else, and I could hardly think of a better way to convey this extremely detailed character sketch.
128. "John Deere Green" by Joe Diffie (#5, 1993-94)
The husband of this newly married couple professes their love by painting their names on a water tower. In this, Dennis Linde finds an unusual yet charming metaphor about the power of love; nothing can seem to cover up the vandalism, nor does anything seem to end the couple's relationship. Who better to give this song to than Joe Diffie, who mixes the right amount of passion and humor into the delivery? It is possible for a novelty song to have a whole lot of heart. A dark green heart with "Billy Bob Loves Charlene" painted inside of it.
129. "Jukebox in My Mind" by Alabama (#1, 1990)
In a truly inspired metaphor, memories of a lost love are portrayed as songs in an eternally-playing jukebox. Just when one is over, the next begins. Alabama's harmonies are as spot-on as ever, and the production is considerably more honky-tonk than they usually leaned, but still somehow perfectly fitted to their style. One by one, every spin of this song takes me back to three-year-old me wandering down the aisles of A&P, singing this at the top of my lungs. And 30+ years later, just realizing how excellently it holds up.
A more feminine take on the unexpected falling-in-love tropes as exemplified by "Guilty". Unlike the Warrens, who find themselves too resilient to commit, she resists because she's been burned before. For now, she's got her radio, a cat, and a TV to keep her company (I have SiriusXM, a kitten, and a playlist of Helluva Boss episodes. Close enough)... and then stumbles into love anyway. Her tone is more lighthearted and playful ("none of that silly love stuff") but has every bit as much character, making it a great counterpoint. In fact, it may even be about the same relationship.
131. "Just to See You Smile" by Tim McGraw (#1, 1997-98)
Just like predecessor "Everywhere," this one excels on understatement. He's doing all of these things just to make her happy. At first it just sounds like selflessness, but then that last line comes up: "So I told you that I was happy for you / And given the chance, I'd lie again." It's so subtle and unexpected (as Mark Nesler co-writes tend to be) that it isn't until the last chorus when you realize this guy is not the one smiling. And there's an underlying contemptuousness that manages to bubble through just enough for you to stop and go "whoa" as the fiddle and steel play out like end credits.
132. "Keep It in the Middle of the Road" by Exile (#17, 1990)
Their first single after losing frontmen J. P. Pennington and Les Taylor (although Pennington still wrote it) brings in new lead singer/guitarist Paul Martin. Already a strong lyrical take on "if it ain't broke, don't fix it," it's greatly escalated with an amazing arrangement. Entirely acoustic but very lively and fast, it also crams in a ton of extremely complex jazz chords and some very bright piano fills. How ironic that a song about sticking to what works does the exact opposite of that musically -- yet is all the better for it.
Danny Frazier has a beautiful operatic voice matched to some finely polished production for a nakedly desperate plea. He doesn't know what specific song just hit a nerve with him; he's begging the DJ to play it and give out his name in hopes that this will bring her back. He's tried just about everything else -- and if this doesn't work, then the title phrase implies that he may commit suicide. That is the kind of darkness we rarely got in the '90s, and it's executed to perfection here. How did these guys only get one album?
Men have played a lot of emotive roles in country music, but rarely of the widower. Evocative lyrics about dust in furnace vents and a third-grade teacher who looks like the now-deceased wife show off Tom Douglas' knack for masterful and emotional storytelling. (Also a shout-out to the extremely well-placed reference to Romans 8:28.) Drew Womack's beautiful singing voice does a lot to enhance this already very strong lyric. We could still have hits with sad songs in 1998, so why wasn't this one a bigger hit?
Ricky Lee and Doug Phelps' departure from the Kentucky Headhunters (Doug has since rejoined) started with a song that hits hard when you least expect it. While the world can get you down to the point of not even wanting to leave your room, sometimes all you need to do is just get out and clear your head. Simple but tuneful, it feels like a fusion of the Byrds and the Everly Brothers. Off-kilter lyrics like "who would think that a boob tube could find such a friend" (or in my case, a DVR full of Tuca & Bertie episodes) add even more personality.
136. "Letting Go" by Suzy Bogguss (#6, 1992)
The folksy yet assertive Bogguss gives us this tender tale of a mother and daughter parting ways when the latter turns 18. The daughter is off with her personal belongings in the first verse; by the second, the mother realizes that she has more free time but still misses her child. Both know what's coming but can't hide their emotions. Bogguss' delivery is pitch-perfect, and the production is far less dated than latter-day Jimmy Bowen tends to be. I could have picked several of her songs, but went with the one that hits emotionally hardest for me.
137. "Life Gets Away" by Clint Black (#4, 1995)
One of his many songs about time stands out not only with its unusual melody and spacious production, but also its central thesis: don't overthink about what you can't control in life. There's a reason you are where you are now. There's a reason I'm a music writer/church organist/grill cook/Wikipedia editor/Wheel of Fortune champion/whatever the hell else I am in a rundown house in rural Michigan, praising my second-favorite Clint Black song. Because with his anthemic delivery of this well-constructed message, I want to follow his advice.
138. "Life's Little Ups and Downs" by Ricky Van Shelton (#4, 1990-91)
RVS always had a knack for finding old forgotten songs and freshening them up for modern ears. This Charlie Rich cut from 1969 gets a read that's as straightforward as it is impassioned. She wanted a dress and both of them wanted to add on to the house, but a lack of money got in the way. Even so, they love each other so much that it hardly matters. Despite the song's age, nothing feels anachronistic or sexist -- if anything, financial strain is all the stronger on couples now. Perhaps that sense of timelessness is what drove him to cover it?
139. "Like the Rain" by Clint Black (#1, 1996)
"Life Gets Away" is my second-favorite, and the follow-up is my favorite. I've always been taken by the, well, raininess of the production. A well-composed Dorian mode melody full of acoustic guitars, piano, chimes, and heavy drums. And that exceptional production is hooked up to a lyric that turns the underlying rain metaphor on its head. He "never liked the rain" until walking through it with the one that he loved, but now he loves the rain and is falling for her just like it. It's that last little twist on the wordplay that really makes me fall for this song just like the rain.
His only top-40 hit was a cover of "Get Rhythm," and the Cash influence shows in his commanding baritone that seamlessly moves from singing to reciting and back. This guy's been manipulated by a lady who tells him that he's the best thing ever, and he's so elusive about how this whole situation makes he feel. Although he says he's "blinded" by the white lies (great wordplay there), he still admits that he'd fall for her again. And it's these conflicting scenarios that make the song all the more fascinatingly enigmatic -- is he the one lying? Does he really want this?
141. "Lipstick Promises" by George Ducas (#9, 1994-95)
George's only top-10 hit as a singer (he's had others as a writer) finds him doing his best Roy Orbison, and guitarist/producer Richard Bennett builds a wall of sound behind him that towers with drums, mandolins, and backing vocals. Add to that a very strong, twisting, Dwight Yoakam-esque lyric about being deceived by an unfaithful woman ("Every single word you said / Every drop-dead shade of red / Were just lipstick promises"), and the result is an extremely compelling style fusion that makes me wonder how this guy didn't have more hits.
A song that I discovered from the cassettes (later CDs) of new songs that used to ship with every issue of the short-lived New Country magazine. (Hi, Brian. Thanks for the magazines.) The line "Listen to your woman when she don't talk at all" is a great lyric about paying attention to the little things to keep a relationship intact. I love the lush production and big vocal performance, along with the reference to Camelot to add a little bit of class to this simple yet well-executed concept. It's possibly the most Rodney Crowell song not to be recorded by Rodney Crowell.
143. "Little Man" by Alan Jackson (#3, 1999)
This song reminds me not only of my aforementioned hometown, but also of Cooper, Texas, where my mom's cousins lived. It's a small farming town whose courthouse square was mostly deserted even in the late '90s, and has only gotten even more barren since. Alan keeps things vividly detailed (there probably still is an old Coke sign in some small town somewhere) and personal, avoiding "back in my day" whininess. He brims with sympathy for struggling small-town business owners losing their livelihoods to the likes of Walmart, Dollar General, and 24-hour convenience stores.
144. "A Little Past Little Rock" by Lee Ann Womack (#2, 1998)
She's hitting the road to get away from her ex -- a theme that has been done before, but rarely this tunefully or emotionally. Sometimes you just need to keep things simple and let the emotions shine, and boy does Lee Ann deliver on that front (I love the term that a review in Billboard used: "lump-in-the-throat vocals"). Strings and baritone guitar to add countrypolitan flair that's kept in check with fiddle and harmonica, but best of all is the dramatic irony of her own ex-husband Jason Sellers singing harmony!
145. "Little Rock" by Collin Raye (#2, 1994)
My dad was an alcoholic until the day he died, and I always understood this to be one of the reasons behind my parents' divorce. So nearly anything that sympathetically portrays people trying to kick that habit is going to catch my attention. The narrator has made a lot of progress, but still feels incomplete because he misses the woman who was driven away by his drinking. A lot of detail is woven into this song (including very tasteful and un-forced Christian imagery), making you believe every word of this story. This was the moment in which Raye became a true artist.
One of the last doses of hardcore country-rock in the first half of the decade. I love the opening line alone: "She was raised in the country in a shotgun shack / The only relief was the house out back". And who is this long-legged Hannah, anyway? She's an attractive truckstop waitress who turns everyone's head -- and she can cook and fix trucks, too. That's quite a lot of brains to match the beauty. Hunter's production and playing are high octane, keeping this song firmly stuck in my head while making me wonder just how he fell off the radar so fast.
147. "Lonely and Gone" by Montgomery Gentry (#5, 1999)
Just like that same year's "All Things Considered," this guy's been dumped. But instead of holding his head up, this guy seems confused and alone as he tries to put the pieces together. Lines like "silent as a tomb" and a call-back to Johnny Lee's "You Could've Had a Heart Break" are the neat lyrical touches one would expect from a song co-written by Pirates of the Mississippi's lead singer. Eddie's impassioned baritone, Troy's high harmonies, and the slide guitar-heavy production create the perfect sonic landscape.
148. "Lonely Too Long" by Patty Loveless (#1, 1996)
A nuanced look back at a one-night stand. The woman points out that the man in the situation shouldn't feel guilty because just like her, he's in an unsatisfying relationship. It's not just a sympathetic cheating situation -- it's also an offer to bail him out if his current situation doesn't improve. Patty's voice is matter-of-fact and utterly non-judgmental, letting the song stand as an exceptional character sketch (although I am curious as to how Doug Stone's unreleased version would have sounded). Her last #1 hit also happened to be her best.
David Lynn Jones almost feels like a more country version of Bruce Springsteen, given his growling voice, heavy production, and working-class themes. Here, the everyday barroom encounter is written to perfection: a Porter Wagoner name-drop, unusual turns of phrase like "jaded hearts" and "neon Romeo," and the thoughtful observation of how "the brokenhearted come to cry for each other". I especially like how the song shifts perspective and reveals the narrator to be one of said brokenhearted. The gritty approach, gently polished with a saxophone without sounding dated, pays off in spades.
A band including former members of Bread, whose music is as boring as their name, should not have been this interesting to me. Best among their singles is their debut, a surprisingly compelling tale of a man who gave up his one true love in favor of chasing his dream to be a musician and is still unhappy over doing so. It'd be incredibly easy to dismiss this with its breezy harmonies and short play length, but I feel that the minimalism lets the whole bittersweet "live and learn" theme sneak up on me when I least expect it.
151. "Look at Us" by Vince Gill (#4, 1991)
John Hughey's high-toned "crying steel" adds a warm tone to this song right out of the gate, and who better to match that than Vince Gill? The lyrics are such a beautiful portrayal of enduring love that even my non-romantic heart is touched every time I hear this. The clear "look at me, look at you" setup doesn't come until the second verse, and there's no chorus, so the song has a very purposeful flow that doesn't waste any time. And it just sounds so pretty! If you want a perfect country romance ballad, just look at "Look at Us".
The Gentle Giant's last hit feels like an extension of "Good Ole Boys Like Me". Instead of his values and idols, though, it's the country itself getting overtaken by growth. It reminds me of my mom's hometown of Grand Blanc, Michigan, a former bedroom community that got engulfed by subdivisions and strip malls. I never thought her childhood home would end up being a block from a Rite Aid pharmacy, or that Walmart would displace the park where deer always seemed to be grazing. And even as progressive as my mindset is, there's still part of me that misses what used to be.
153. "Lost and Found" by Brooks & Dunn (#6, 1992)
The first of only six singles in B&D's career to let Kix sing lead, and Exhibit A on why there should have been more. A lost-love lyric and plaintive vocal are perfectly fitted to that "desert sky" style of production I mentioned way back at "Even the Man in the Moon Is Cryin'". She's mysteriously gone, and he's out looking for her -- but nobody knows where she is. Even though her car's still in the driveway. That hook "like a lost and found in a border town" just gives such a concrete and unusual image that slots so squarely into the story.
154. "Love Like This" by Carlene Carter (#70, 1995)
The power of love can be so strong as to do just about anything. It's a common theme, but the underrated duo of Mary Ann Kennedy and Pam Rose (who originally recorded it as Kennedy Rose) came up with some oddly incisive lyrics like "warriors have laid weapons down" as well as a completely unexpected modulation on the last line of the chorus. Carter's performance is as fiery as ever, bolstered by Howie Epstein's guitar-heavy production -- and she even works in another key change at the end for good measure.
I would have put this one on the list for the lush, Celtic-tinged production alone (is this the first country song to use a pennywhistle?). But it's made ten times better by a great slow-burner lyric about two separated lovers. It's not until the third verse that we even find out that he's found someone else; while she's glad that he's happy, her torch for him still hasn't been snuffed out yet. Add in offbeat references to moonbeams and trapeze artists and the result is a long, winding musical journey that just gets more enjoyable on every listen.
156. "Lucky Moon" by The Oak Ridge Boys (#6, 1991)
Again, I like the Oaks too much for my own good. Their last hit finds a man pleading for one more chance at salvaging his relationship. He found this out by subtly eavesdropping a phone conversation she's having with a friend, but his tone never seems whiny or prying. He just sounds like he casually overheard enough to realize the error of his ways, and even goes so far as to set up a pleasant surprise for her. I think I just really like this song's subtle moment of realization, and the harmony-driven arrangement certainly doesn't hold it back, either.
157. "Mama Don't Forget to Pray for Me" by Diamond Rio (#9, 1991-92)
Diamond Rio's mandolinist Gene Johnson once said of this song, "if you're gonna touch someone, touch them with something that's positive." Recently during one of my downward spirals, I heard this song on the radio for the first time in ages, and texted the lyrics to my mom. She then listened to it too, and we both felt better afterward. I think Gene, and the rest of his incredibly talented band, were right. And even without that personal connection, it's an extremely well-told, likable story and a great use of Diamond Rio's always flawless musicianship.
158. "Man! I Feel Like a Woman!" by Shania Twain (#4, 1999)
I struggled to think of which Shania songs to put on here, and ultimately went with one of the obvious choices. But for good reason: it's one of the goddamn catchiest feminist anthems out there (that intro alone hooks me right in immediately), and it's as playful and witty as it is empowering. Far more than almost any other girl-power song, it's also the one that I've found grown-ass men such as myself singing along to in total sincerity. And that's perhaps its greatest asset: for at least three minutes, any music fan of any gender can experience the completely boundary-free joy that this song brings.
True love can strike at any time and place. The two protagonists fall in love on a carousel at the county fair, and then grow up to watch their kids play on that same carousel. (I'm a sucker for good wordplay, and "watchin' me and Mary go 'round" is a winner.) By keeping the sound understated, the wordplay and vivid imagery (how many other songs even used the word "calliope" or mention the Jeep Wagoneer?) come right to the forefront, resulting in a song that catches the brass ring when you least expect it.
160. "Matches" by Sammy Kershaw (#22, 1998)
The barroom encounter starts off normally -- he lights her cigarette with a match, and she writes down her number in the matchbook. They hook up and then break up, and he finds his house empty except for said matchbook. So what does he do? He uses the matches to burn down the bar where they met! This plot twist is so unassuming, especially given Kershaw's mellow read, that it might not even hit you until the song's over: "Wait, he did what?!" And I love it when a song catches me off guard like that. Yet again Skip Ewing nails an unusual premise so unassumingly.
Jason Sellers is usually a pretty damn good songwriter and backing vocalist, but his two '90s albums found him surprisingly comfortable in a starring role too. His extremely likable second (and final) solo album brims with positive energy, as exemplified by the lead single. Sounding like a harder-edged Bryan White (and backed by a then-unknown Jamie O'Neal and some fine harmonica playing to boot), he lays out a great lyrical trick: this dream girl that he's gushing about so much (her eyes, her hair) is all in his head. But he's so convinced that he'll find her someday that it's hard not to root for him.
162. "Maybe He'll Notice Her Now" by Mindy McCready featuring Richie McDonald (#18, 1996-97)
Mindy compares herself to an unnoticed painting on the wall, which she then takes down and replaces with a goodbye letter. Sure enough, he notices the absence of both painting and woman, and ends up reconciling. Mindy's voice finds a sweetness and vulnerability that you wouldn't expect from the same person who did "Guys Do It All the Time" (especially when she reveals at the end that she was the narrator all along), and Richie (back when neither he nor the rest of Lonestar sucked) makes a great harmonic partner.
163. "Maybe I Mean Yes" by Holly Dunn (#48, 1991)
Perhaps my most loaded pick. While I do sympathize with anyone who felt that this song's lyrics condoned date rape, I don't believe that to be the intent of the song whatsoever. The lyrics' playful flirtatiousness suggests that the woman is intentionally being self-contradictory just to troll whoever's trying to make a move on her. And the edgier vocals and production (seriously, what a leap from "Daddy's Hands" in that regard) read to me as so confident and in-control that if anything, I see this song as another great example of how increasingly feminist country music was getting in the '90s.
164. "Maybe It Was Memphis" by Pam Tillis (#3, 1991-92)
Every single thing about this song is perfect. The spacious, electric guitar and backing vocal-heavy production sounds like almost no other country song. Lyrical references to katydids, Glen Campbell, and porch swings clearly lean Southern, but the name-drops of William Faulkner and Tennessee Williams class things up immensely. Pam's bold, clear vocal rises above it all to completely sell the story. We learn so much about the encounter in just three verses and a simple chorus, but the result is distinctive, poetic, and timeless.
165. "Midnight in Montgomery" by Alan Jackson (#3, 1992)
A story about meeting Hank Williams' ghost could be gimmicky at best and self-serving at worst, but Alan does it up to extremely convincing effect. Not much comes from the encounter, but the atmosphere is so compellingly haunting ("see the stars light up the purple sky / Feel that lonesome chill" being a particularly strong example here) that you're led to believe every note of it. And the fact that we don't even find out who the ghost is until the last line is just another example of the winning suspense.
The rush to find the next Brooks & Dunn tapped the two writers of "I'm Over You" and got unexpectedly strong results. Drive-in theaters, a longtime fascination of mine, are great settings for nostalgia. This one uses emotive vocals and cute lines like "I'd reach out and pull her close / As Godzilla conquered Tokyo" to tell of its lost love in a very un-formulaic, impassioned manner. I'd like to think that after the drive-in closed, he watched it get overgrown with weeds and then torn down for a convenience store -- you know, much like the one in my town did.
167. "My Heart Has a History" by Paul Brandt (#5, 1996)
This guy knows his own track record for being a heartbreaker, and warns a prospective lover of this right away -- even though he has a feeling that she might be the one to break the pattern and finally straighten his wayward mannerisms. By not posturing and leaving himself even somewhat open, and by pushing his vocals into his criminally underused lower range, Paul finds an extremely compelling mix of conflict and vulnerability. Sometimes the best option is to just let down your guard and admit your faults.
168. "My Wife Thinks You're Dead" by Junior Brown (#68, 1995)
Junior Brown could have been big in the '70s doing truck-driving country (he did, after all, cover Red Simpson), or in the present day alt-country/Americana scene. His fine picking and commanding baritone add so much to every song, but the best out of a catalog that I wish was bigger is this one. She's apparently done something quite unsavory in his absence, and he's married to another woman who's been convinced that said ex is dead. The whole exchange is so wryly twisted as to keep me amused literally every time I hear it.
169. "Neon Moon" by Brooks & Dunn (#1, 1992)
While the lyrics alone are wonderfully evocative in their portrayal of a brokenhearted man drinking alone in a bar, it's Ronnie's perfectly country voice and the production that really heighten things here. The sound is spare and somber, making the song sound just like a smoky, dimly-lit bar whose only patron is a downtrodden man slumped over a warm, half-finished beer (although Ronnie has joked that it would actually be a Diet Coke). When one's broken-heartedness conveys such strong imagery, I can't help but feel sorry for the guy.
170. "Never Again, Again" by Lee Ann Womack (#23, 1997)
Right out of the gate, Lee Ann brought a delightfully throwback approach. Billboard rightly compared this to Loretta and Tammy, but I've always detected more than a hint of Dolly in LAW's material as well. Just like the retro inspirations, the lyrics say a lot with few words, making all the clearer her regret over an on-again/off-again relationship. Lines like "I must be addicted to your kind of love" add humor to the pile of emotions, leaving me with no question as to why this, despite its low chart peak, is so well-remembered. (Especially by whoever programs SiriusXM's "Prime Country" playlist.)
Fun fact: unique song titles instantly add 10% to your chances of making this list. This song has a crisp production style that was made for radio, performed with infectious energy that could only come from a Louisiana-based band. The title references Nickajack Lake, a reservoir formed by the Tennessee River outside Chattanooga. That one random love found off I-24 one day near the Georgia line (turns out it worked; they're now married and have kids!) is compared to the formation of said reservoir. In short, it's a clever simile delivered greatly, and it's fun to say the title.
172. "The Night's Too Long" by Patty Loveless (#20, 1990)
My favorite Patty Loveless song is one of many on this list where a woman takes control of her life. By putting her money where her mouth is, the waitress in this song successfully moves to an office job in the city and snags the man of her dreams. Unlike most such songs, there's no implication that she misses her upbringing whatsoever; instead, the song goes out of its way to prove that she was meant to be in the city. Sometimes things just work out if you take a chance: the narrator of this song by chasing her dreams, and Patty by cutting a Lucinda Williams song.
One of the only times that Boomer pop culture is anything but nostalgic. This young married man struggles for success as he watches the world rapidly change around him. By realizing that "age of innocence" and "peace and love" aren't all they're cracked up to be, he adds an unusual degree of jadedness before ending somewhat positively on the phrase "Somehow we got by in 1969." His thesis on the passage of time may be tied to a specific generation by name-drops of Vietnam and CCR, but the central emotion is instantly relatable to almost anyone.
174. "No Man's Land" by John Michael Montgomery (#3, 1995)
So many country songs push anti-divorce sentiment so strongly that it's refreshing to see one where the divorcee is portrayed in a positive light. The woman in this song, despite a mix of emotions over her split (exhaustion, poverty, loneliness, confusion over what went wrong), still presses on because of how much she loves her children. Even if I weren't raised by a struggling divorced mother myself (something which led me to get this song played as a listener request on Bob Kingsley's Country Top 40 in 2006), this song's gently supportive tone would still win me completely over.
175. "No News" by Lonestar (#1, 1996)
By setting the scene (she wants to find herself; he's an "understanding guy" who picks up the slack but has lost contact with her), the chorus' litany of quirky ways she could contact him hits all the harder. And then we get the equally witty coda listing off possible scenarios as to where she might even be. Add to it some hard-hitting production and the early version of Richie that actually had some grit and wit to his voice, and I'm left wondering how we went so quickly from this to garbage like "I'm Already There".
176. "No One Else on Earth" by Wynonna Judd (#1, 1992)
I swear, this wasn't just an attempt to get every Jill Colucci co-write on here. What this is, however, is a song that has an extremely distinctive sound from the first note. Slap bass and heavy reliance on ride cymbals make the song considerably bottom-heavier than the norm, and Wynonna's distinct voice leads us through another "I didn't think I'd fall in love until I found the right one" story. Lyrics like "burning me alive" and "weaving a weak alibi" add to the surroundings, helping to make this one extremely groove-heavy yet unexpected trip straight into love.
177. "No One Needs to Know" by Shania Twain (#1, 1996)
She's in love, but she wants to keep it a secret. It's a cute lyric with a lot of charm: "Am I dreaming or stupid? / I think I've been hit by Cupid" is just a great opening line. She's making all these plans down to the kids and pets, and she isn't lonely anymore because she's got everything lined up so perfectly. There's only one catch: the guy doesn't know yet! It's an unexpected nuance to a concept that could easily become too cutesy in other hands. But the sheer happiness and twanginess of the production make it a winner.
Mattea's poppiest album still keeps her direct, folksy strengths intact. It's another wanderlust song, but instead of being upbeat and anthemic, there's an odd sense of melancholy that seems to creep in at times. In that sense, it seems to be reflecting the present -- the "I want to get away" mood -- moreso than the excitement of getting away proper. Between that and lyrics like "a red light blinking on an empty street," I feel every note of the everyday small-town boredom she wants to get away from, and I want to take that one-way train ride with her.
179. "Now I Know" by Lari White (#5, 1994)
I thought for sure I'd never get over you, but I did. It's a bit of a different premise already, but I like how it builds up slowly, not hitting "I always wondered how I'd live without you / Now I know" until nearly a full minute in. Lari seems to know that her full recovery from a breakup isn't the norm, but her delivery (matter-of-fact on the verses, anthemic on the chorus, confident on everything) makes it clear that, like so many other female country singers in the '90s, she's the one in control. That, and I just love it when an artist's biggest hit is also their best.
180. "Now That's All Right with Me" by Mandy Barnett (#43, 1996)
The first voice behind the musical Always... Patsy Cline seems like the best choice to convey a song that feels like Cline's well-aged no-nonsense approach freshened up for the '90s. There's a sense of youthful energy underneath it all, giving the right bearings for a song that takes a wide-eyed look at falling in love ("We're wild and we're young and we're free to love"), but a maturity and polish that comes off as more mannered than, say, Lila McCann's "I Wanna Fall in Love". These Kostas co-writes seem so simple and radio-friendly on the surface, but become more nuanced on closer inspection.
A left-field choice for sure, but I stand by it. By combining Inuit musical influences with a modern country-pop approach, she manages to find a sound that is both personal and culturally significant. The lyrics may seem simple on paper in their stands against racism and prejudice, but her crystalline singing is equally convincing in both English and Inuktitut (and either way, "fires of freedom" is just such a neat yet evocative metaphor). It's a common but necessary message, and she understands the power of personalizing that message.
182. "O What a Thrill" by The Mavericks (#18, 1994)
Yet another Roy Orbison influence arises... Raul Malo is probably one of the closest matches to that style (although not for lack of effort on the part of James House, who did the original version in 1989 and backs the Mavericks here). This guy doesn't want to blow his chance at reconciliation ("Oh, once you, you were my baby / You're my baby still" says so much with so few words), and Raul and his bandmates perform the hell out of it. By keeping the lyrics simple, the emotion and production rise to the forefront, and both are enough to make the "stars stand still".
183. "On a Bus to St. Cloud" by Trisha Yearwood (#59, 1995-96)
Like I said at "Everywhere," it's common to be haunted by the image of your lover after they have left. Just like that song, this one lists off possible destinations all over the country. But the second verse reveals what exactly happened to the person behind this "face in the crowd" -- he committed suicide, and she is still completely distraught over this. Trisha's vocal reaches Alison Krauss levels of haunting etherealness, and the pretty, piano-heavy production is a perfect match for this devastating, beautifully sad story-song.
184. "On the Road" by Lee Roy Parnell (#6, 1993)
My favorite country song. Every single ingredient hits home for me -- Lee Roy's bluesy vocals and slide guitar, the otherwise melancholy production, and of course the lyrics. Three different examples are given of people using a road trip as a means of finding themselves, all richly detailed and fascinating. This song came out right between two of my biggest childhood road trips (one to Wisconsin, one to Disney World). When I hear it, I think not only of those trips, but of just how much joy I get from traveling to this day Because if it's anywhere, you'll find it on the road.
185. "On the Verge" by Collin Raye (#2, 1997)
"If I'm not in love, I'm on the verge" is the kind of hook that I would expect out of the extremely underrated Hugh Prestwood. I especially dig the plucky guitar work throughout the verses, seamlessly leading into the smooth, big chorus -- as if musically suggesting all of the bubbling-under emotion of "I didn't think I was going to fall in love" present in the verses is now bursting out into the killer hook. Raye could hit extremely hard with heavy material like "Little Rock," but songs like this show him every bit as adept at selling the hell out of the lighter moments too.
"Achy Breaky Heart" cast such a huge shadow that it's easy to forget Cyrus' skill with more downbeat fare. One such example is this beautifully moody, wistful look at a relationship that's not working out. The narrator knows the end is coming and takes it all in stride. He just wants to have one last reminder of what they had before they part ways. Cyrus finds a tenderness to soften some of the rougher rock edges of his voice, giving a very passionate read of this surprisingly nuanced breakup-to-be. How did this song not even chart?
I love Lorrie Morgan. She has a pretty, commanding, colorful voice that had few rivals in the '90s. While she didn't often match it up to harder production, the results when she did are extremely compelling. Electric guitar and drum-heavy, minor-key production matches up to her bracing demand for a night on the town. I especially like just how many rhymes the chorus comes up with for "tonight" without any of them feeling contrived, and just how intensely the whole package is performed. As much as I dig Lorrie, I would have liked to see her kick up her heels a bit more often like this.
188. "One Way Ticket (Because I Can)" by LeAnn Rimes (#1, 1996-97)
LeAnn Rimes succeeded where most teenage artists have failed: by having a clear musical image, and strong songs that (usually) weren't cutesy or watered-down. Young or old, wanderlust is a relatable theme -- whether it be getting away from a lost love (as this song seems to be hinting at) or just getting comfortable with increasing maturity (an unintended sub-theme that probably cropped up from the age of the singer), the song hits all the right notes through an energetic performance that was done entirely in one take.
What would you get if you mixed Roy Orbison, Johnny Cash, and Steve Earle, and sent them to Canada? I'd have to say the answer would be Prairie Oyster. A big, reverberant baritone guitar riff and steady beat drive this song just like the train on a one-way track that's being sung about. There are so many songs about leaving the country for the city, and then missing the country -- only in this case, the country is too rundown to stay there, and the city life ends up killing the main narrator. It's a surprise ending to this common trope, and it's extremely compelling from the first note to the last.
190. "Only Daddy That'll Walk the Line" by The Kentucky Headhunters (#60, 1991)
Yes, I know this was only a honorable mention on my top-ten list. But if that list were limited to singles, then this would have been much higher. The Headhunters always excelled at covering classic country and rock songs alike, by rocking them out as hard as they could. And an early Waylon Jennings cut is a great jumping off point. She's packing up to leave, he's sick of her misbehavior, but still holds fast that anything else would be a mistake. There's an angry energy to the proceedings that is extremely befitting an up-to-eleven approach, and the Headhunters more than deliver on that front.
191. "Only the Wind" by Billy Dean (#4, 1991-92)
The narrator was scared by the noise of a wind storm as a child; now an adult, he's scared by an impending breakup. While he had emotional support in the first scenario, he clearly doesn't in the second. It's an interestingly done parallel, helped by some subtle breaks from verse-chorus-verse-chorus structure and a moody, reverberant production that calls to mind the wind storm being sung about. Dean seems to understand that being scared and vulnerable doesn't make you any less of a man; if anything, it makes you more human.
192. "Outbound Plane" by Suzy Bogguss (#9, 1991-92)
Kathy Mattea wasn't the only one who struck gold covering songs by the late great Nanci Griffith, it seems. Already a great lyric, Bogguss sells it with her always pitch-perfect country-folk vocals. The man's offered one last chance to reconcile before she leaves for good, and sure enough, she boards the plane when he doesn't take up the offer. (I especially like how she points out that she doesn't care whose fault it is.) The unusual setting and sense of resolution really give a sense of, well, takeoff for this song.
193. "Past the Point of Rescue" by Hal Ketchum (#2, 1992)
Another thing that Kathy Mattea wasn't alone in doing was drawing influence from Celtic music. This cover of a song by Irish singer Mary Black keeps all of the charm of the original (a delightfully self-aware look at a relationship on the brink) and seasons it generously with country, folk, bluegrass, and even rockabilly. It's a move that shows a knack for doing a cover song to perfection, and for adding a dash of class and thoughtfulness that easily put Hal in line with some of the other highbrow country-folk powerhouses like Rodney Crowell or Mary Chapin Carpenter.
194. "Phones Are Ringin' All Over Town" by Martina McBride (#28, 1996)
I bet you're surprised by all the Martina songs on a best-of list, huh? This may be one of the only country songs about what would now be called "ghosting". She's skipped town because of his cheating, and he is desperate to try and find her again through any means possible (even her sister's house and her hair salon). But it's too late, as she's taken a plane (I love it when consecutive entries have a thematic connection like that) to get away from him. Much like "Outbound Plane," it succeeds by giving a sense of finality.
Clinton Gregory managed to hit the charts quite a few times for an indie artist, and I think it was his constant quality that saw him making so many visits. Lyrically, this one seems very simple -- it is at its core just a song about a hot piano player. But damn it, I'm a piano player too. And this one's reliance on a very driving and unusually electric arrangement that still sounds super-country (read: Wurlitzer keyboard and electric fiddle) gives it a sonic element that jumps out of the speakers every time I hear it. Do you know how hard it is to outdo Conway Twitty's version of a song?
Maybe it's the melancholy production and the way it leans into the iv chord. Maybe it's the throaty, plaintive vocal heightened with twin-sister harmony. But this has always been to me one of those "our relationship's dying and I want to save it" songs far greater than the sum of its parts. ("True love has no pride" is a pretty damn good lyric, too.) This one just hits all the feels in a way that just has a markedly different texture than almost any of its competition. I think if it weren't for them debuting at the same time as the then-Dixie Chicks, they might have been a force to be reckoned with.
197. "Postmarked Birmingham" by Blackhawk (#37, 1997)
Is this the only time that Ramada Inn has ever been name-dropped in a song? Either way, this is a greatly detailed breakup. She just leaves him with a single letter that offers no clues other than its postmark. He's got a lot of questions as to where she's gone and why. But unlike "No News," the tone is serious and conversational, desperate at times. Blackhawk excelled by merit of a distinctive lead singer, tight harmonies, and song choices so exceptional that this isn't even their only entry on this list. (Spoilers.)
The song that introduced me to this comedic talent. Instead of being an exercise in macho posturing, this handyman-wannabe protagonist is a well-intentioned goofball who just wants to have fun and make life easier (unintentionally paralleling Tim Taylor and Red Green, both of whom also debuted in 1991). Add in some witty spoken asides, and the result is delightfully subversive and funny enough to withstand repeated listens. (We'll just forget that this is the same album with the jaw-droppingly offensive "Workin' for the Japanese"...)
199. "Put Your Heart Into It" by Sherrié Austin (#34, 1998)
I love how the album version begins with backing vocalist Donna McElroy snarking at Sherrié, "you're too young to know what this song's talkin' about!" But the groovy guitar riff and Austin's vocal show that she indeed knows what she's talking about after all. You don't need to do all of this crazy stuff like pop out of a cake or spell it out in skywriting; just cut the crap and love me! The song is bursting with a youthful energy that more than suits the lyrics, and makes me wonder how Austin never managed to score a hit. What's that? "Streets of Heaven" you say? LA LA LA I CAN'T HEAR YOU.
200. "Queen of My Double Wide Trailer" by Sammy Kershaw (#7, 1993)
The redneck protagonist is having a good time with his sweetie when some guy named Earl takes her away -- only for the narrator to swoop in and take her back with the offer of onion rings and TV. As yet another Dennis Linde song, quirky details abound in such lines as "he's the Charlie Daniels of the torque wrench". Those details work with the uneven time signatures (also a Linde trademark) and Sammy's reedy deadpan for an extremely memorable, enjoyable exchange. Plus, if it weren't for this song, we wouldn't have "Goodbye Earl".