400 Best Contemporary Country Singles: #375-#351

The 400 Best Contemporary Country Singles
Part 2:

“Take It Back”
Reba McEntire
Peak: #5

For a singer defined by weepy ballads, McEntire is remarkably brass on this jazz-tinged kiss-off number. She approaches the song with ferocious intensity, making it one of her most fearless performances ever.

“The Last Thing On My Mind”
Patty Loveless
Peak: #20

She’s best known for her mountain twang, but Loveless proves she can wrap her voice around a pop melody as well as any of those city singers. This single is one of her most underrated performances.

“She’d Give Anything”
Boy Howdy
Peak: #4

It would be another four years before single women would receive their definitive country anthem, “All The Good Ones Are Gone.” Until then, they had to make due with this above-average single by a very below-average country band.

“Tender When I Want To Be”
Mary Chapin Carpenter
Peak: #6

For an artist defined by her knowing cynicism, this optimistic love song is a refreshing change of pace. Carpenter sounds like she’s channeling Jackie DeShannon, circa 1965.

“There’s More To Me Than You”
Jessica Andrews
Peak: #18

She became a star when she was in her early teens, but she finally came of age with this breakup hit that was released in two separate versions: an uptempo, rocking take, and a soft piano ballad. Andrews shines in both settings.

“Do You Want Fries With That”
Tim McGraw
Peak: #5

An ex-husband confronts the man that’s taken his place, demanding respect and appreciation for “paying both our rents.” It could’ve been a classic country weeper, if the setting wasn’t at a McDonald’s Drive-Thru window. Tim manages to make a potentially pathetic narrator seem sympathetic with his snide delivery.

“This Side of Goodbye”
Highway 101
Peak: #11

One has to wonder how many more great records radio would have played from Highway 101 if lead singer Paulette Carlson hadn’t left for an ill-fated solo career. While this doesn’t reach the dizzying heights of their pre-1989 singles “Cry, Cry, Cry” or “Whiskey, If You Were A Woman”, the depth of this performance suggests they still had a lot more great music left in them.

“Back on the Farm”
The Thompson Brothers Band
Peak: #58

It received more attention for it’s cheeky video, full of steaming cow pies and seductive sheep, but this country-rock single suggested what Steve Earle would be doing in 1998 if he had stuck with mainstream country. The combination of acoustic twang and heavy percussion sounds normal today, thanks to Big & Rich, but these guys were way ahead of their time.

“I Guess You Had To Be There”
Lorrie Morgan
Peak: #14

While most country women of the 90’s were singing strong-willed, independent anthems, Morgan spent a good portion of her catalog harking back to the Tammy Wynette-style country weeper days. This tale of a woman confronting her cheating husband ends with a sad resignation: “We’ve drifted so far apart, and it’s hard to admit it but there’s nothing left for you here, so I guess you had to be there.” Wynette herself said that this single, along with Pam Tillis’ “Do You Know Where Your Man Is”, were the only two songs on country radio in 1993 that she could see herself singing.

“Honky Tonk Badonkadonk”
Trace Adkins
Peak: #2

For those of you, like me, who aren’t sure at first what a “badonkadonk” is, Adkins gives you a hint when he says “Lord have mercy, how’d she even get them britches on, with that honky tonk badonkadonk?” Yes. It’s a song about a woman shaking her ass on the dance floor. Hip-hop culture and vocabulary is seeping into country music. Whether that’s a good thing or not is open to debate, but this record certainly proves that the trend exists. And it’s catchy as hell.

Peak: did not chart

Marcel is a better songwriter than singer; his voice is high-pitched, wimpy and thin. That works perfectly for this song, however, a heartfelt plea for the love of his life to follow him to Tennessee if she thinks she needs him. His sharp attention to detail – “And then a postcard fell from the book you gave me on my birthday”, for example – makes for a very realistic audio road trip.

“Trying to Find Atlantis”
Jamie O’Neal
Peak: #18

O’Neal returned after a long absence with this ode about the difficulty of trying to find the perfect man. She sings without a hint of desperation – about an archaeologist, she sings “I was digging on him, but he wasn’t on me” – and she sounds like if she never does find this perfect man, she’ll be just fine.

“The Good Stuff”
Kenny Chesney
Peak: #1

A classic story-song that manages to tell the entire story of a life-long marriage that ends in the death of the wife by just remembering small details like “eating burnt dinners the whole first year, and asking for seconds to keep her from tearing up – yeah man, that’s the good stuff.” Country music at its best.

“Every Time She Passes By”
George Ducas
Peak: #57

They just don’t make rockabilly records anymore, but at least some people keep trying. Ducas put out this fantastic Orbison-flavored record and country radio yawned, but it still sounds as fresh today as it did nine years ago. It’s worth seeking out if you can find it.

“Don’t Worry ‘Bout A Thing”
Peak: #7

A story of resilience against Music Row criticism shouldn’t be the basis for a great song, but despite very specific references like being in bed with Mickey Mouse, a snarky swipe at their Disney-owned label Lyric Street, the girls manage to make this appeal to keeping a stiff upper lip sound universal. Perhaps because we’ve all “sat ourself down when the seat is all wet.”

“Party For Two”
Shania Twain with Billy Currington
Peak: #7

Cheesy, over-the-top, frivolous and good-natured fun. Twain has always wanted her music to be escapism, a way to forget your troubles. Great records like this prove she’s an expert at it.

“If You Don’t Wanna Love Me”
Cowboy Troy featuring Sarah Buxton
Peak: did not chart

The chorus of this song is one of the most beautiful and haunting things I’ve ever heard. As I wrote once before, this sounds less like a hick-hop song and more like one of those old spoken-word country hits of days gone by.

“The Love That We Lost”
Chely Wright
Peak: #41

“Going through old dresser drawers, fumbling through these closets, I know it’s ’round here somewhere, it’s got to be here somewhere…” So begins this appeal of a wife to her husband to help her find “the love that we lost.” If Wright was a more bombastic vocalist, this would have sounded too maudlin, but she pulls this off with sincerity; it’s the first of a few great singles she’ll eventually release.

“Pour Me”
Trick Pony
Peak: #12

The debut single of Trick Pony sounds like it’s going to be a sad song, as the first few lines sound like a woeful “poor me, poor me.” Then the snare drum kicks in and you realize you’ve been tricked by a homonym. She’s really singing “Pour me, pour me another shot of whiskey.” Surprising on the first listen, still entertaining four years later.

“Small Town Saturday Night”
Hal Ketchum
Peak: #2

Ketchum spares us the glorification of small-town life, painting a realistic but still-loving picture of teenagers killing time on a small town Saturday night. Then again, when he sings “got a six pack of beer and a bottle of wine, gotta be bad just to have a good time” – he’s really singing about teenagers everywhere, isn’t he?

“Sometimes She Forgets”
Travis Tritt
Peak: #7

The female characters in songs by honky-tonkers are usually two-dimensional and wholly unbelievable (see: the entire Brooks & Dunn songbook). How refreshing it was to have Tritt cover a fantastic Steve Earle song about a woman who has been hurt so many times that she’s sworn off men, but sometimes forgets that vow. This is Tritt’s most subtle performance to date.

“Wake Up Older”
Julie Roberts
Peak: #46

For one track on Roberts’ hugely overrated debut album, she actually matches the hype. This bitter tale of drinking to forget and having sex for revenge spares no punches. Lacking the irritating earnestness of the rest of her debut, she shows glimmers of potential here.

“Die of a Broken Heart”
Carolyn Dawn Johnson
Peak: #52

Johnson made her mark as a songwriter first, penning hits for Chely Wright and Pam Tillis. Here, she returns to her roots with a sparse and sad meditation on dying alone.

“Nothing On But The Radio”
Gary Allan
Peak: #1

Allan’s voice is a perfect match for this saucy late-night hit. A fresh take on one of the oldest themes in the country music songbook.

“It Only Hurts When I’m Breathing”
Shania Twain
Peak: #18

For an artist defined by peppy up-tempo hits and romantic ballads, Twain is surprisingly effective doing a break-up song. This melancholy plea that she’s really doing fine after the break-up – it only hurts when she’s breathing – is heartbreaking.


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