400 Best Contemporary Country Singles: #400-#376

Sixteen years ago, country music entered its modern era. The Class of 1989 – Garth Brooks, Clint Black and Alan Jackson among them – ushered in new levels of sales, media exposure and even production quality. The fortune of the genre has gone up and down over the past few years, but never come close to receding to pre-1989 levels of success. Country has remained a genre of multi-platinum sales, radio stations in the thousands and arena-filling concerts.
The modern era of country music is so different in terms of content and style from the ones that preceded it that many of the biggest stars of the 80′ s were nowhere to be found by the early 90’s.

The following list, which will be posted in 16 installments, attempts to evaluate the best singles that have been released since the boom began, without burdening comparisons to the untouchable classics of days gone by. There’s plenty of room for debate about what is and isn’t on the list – John Michael Montgomery and Neal McCoy fans can tune out now, since they’re not going to be making an appearance – but a historical discussion of this era is long overdue. I look forward to hearing about everything I got wrong (and right). Included with each entry is the song, artist, year of release and peak on the Billboard Country Singles chart.

The 400 Best Contemporary Country Singles
Part 1:

“I Play Chicken With The Train”
Cowboy Troy featuring Big & Rich
Peak: #48

An audacious fusion of country and hip-hop – Troy calls it “hick-hop” – this mind-bending collision of genres may be the most eyebrow-raising record to ever hit the country charts. Despite a lukewarm response from radio, Troy’s debut album is nearing gold and reached #2 on the country albums chart.

“We Really Shouldn’t Be Doing This”
George Strait
Peak: #4

Speaking of eyebrow-raising, when Strait debuted this Jim Lauderdale song on the CMA’s a few years ago, the audience shot of Reba McEntire’s face was priceless. This Cajun-flavored romp, with Strait singing in a deeper register than he almost seems comfortable with, is so ballsy and against type that it reveals why Strait remains leagues ahead of his many imitators.

“Ten Rounds With Jose Cuervo”
Tracy Byrd
Peak: #1

The sing-along bar anthems have gotten out of hand lately, but when done with the right combination of spirit and wit, with lines like “The singer couldn’t carry a tune in bucket”, they can be very entertaining. It helps that Byrd’s vocal is completely believable; he actually seems to get a bit drunker with each round. Perhaps José was making the rounds during the recording session?

“Whatever You Say”
Martina McBride
Peak: #2

The verses are sung in an almost-whisper; the chorus is an explosion of vocal power, releasing all of the built-up tension. She’s been repeating the formula to death lately – “How Far” and “Where Would You Be” are essentially the same song – but the original still packs a wallop.

“Trashy Women”
Confederate Railroad
Peak: #10

Before Jeff Foxworthy played the redneck thing to death, Confederate Railroad was the best celebration of an often-mocked lifestyle. I realize he’s singing about trashy women from below the Mason-Dixon line, but every time I hear this song, I picture girls from New Jersey. Got Aqua Net?

“Wild Love”
Joy Lynn White
Peak: #73

The vocal powerhouse that never made it to the big time, White sings the fire out of this Dennis Linde song that was written especially for her. Shania hadn’t made country radio safe for sexy, strong women yet , and this fell on deaf ears. But her cocky style lives on in the vocal stylings of Dixie Chick Natalie Maines.

“Wish I Didn’t Know Now”
Toby Keith
Peak: #2

Right from his debut album, Keith demonstrated a knack for clever songwriting – “I wish I didn’t know now what I didn’t know then.” He realizes he can’t be with the girl who has been cheating on him, but still longs for the days when he didn’t know any better. A very realistic slice of life.

“Right Where I Need to Be”
Gary Allan
Peak: #5

California country-rock was perfected by Dwight Yoakam, and Gary Allan is the first true musical child of the style Yoakam refined. His voice has a raspy edge that’s a cut above the boys that Nashville churns out. This record is driven by a raw Bakersfield energy.

“That Don’t Impress Me Much”
Shania Twain
Peak: #8

With it’s snarky references to Brad Pitt and rocket scientists, this was the hit that turned Twain’s Come On Over from a mega-hit to a phenomenon. The pop fans who weren’t around for “Any Man Of Mine” were surprised to find the pretty ballad singer had a sharp wit to boot.

“State of Mind”
Clint Black
Peak: #2

It starts with an ass-kicking, harmonica-fueled jam session that lasts nearly a minute; radio chopped that part off, and most of America only heard the rest of the song, which is a beautiful celebration of how a good song can completely change your “state of mind.”

“What If I Do”
Mindy McCready
Peak: #26

Her boyfriend’s trying to get in her pants, but Mindy just wants to enjoy the movie. “What If I Do” is structured as a running debate within Mindy’s head about whether or not she should “give in.” One of the most ridiculous songs I’ve ever heard, and equally entertaining. She’s the only artist in country music history who could pull this off.

“You’re Still Here”
Faith Hill
Peak: #28

A gorgeous, string-drenched ballad sung to a person who has passed on. The lyric is vague enough to suggest she could be singing about her husband or her father. One of her most underappreciated gems.

“You Can Depend On Me”
Restless Heart
Peak: #3

The quintessential 80’s country-pop band puts out a little bluegrass-flavored number that’s better than any of her crossover hits. The rise and fall of the harmonies is awesome.

“The Bride”
Trick Pony
Peak: #27

Think about it. If you are single, after graduation there isn’t one occasion where people celebrate you … Hallmark doesn’t make a “congratulations, you didn’t marry the wrong guy” card. – Carrie, Sex & The City

They may not make a Hallmark card, but Trick Pony made a great record about it. The singer couldn’t be any more happy to be attending the wedding of her ex, and can’t help but enjoy knowing she dodged a bullet.

“Never Let Him See Me Cry”
Ronna Reeves
Peak: #73

If Joy Lynn White came to the party too early, Ronna Reeves got there too late. Her thin voice and “I’m a doormat” material rendered her outdated right out of the starting gate. A country scene dominated by strong women like Mary Chapin Carpenter and powerhouse vocalists like Trisha Yearwood had no room at the table for a Holly Dunn-type newbie. But Reeves managed to find herself one good song over the course of four albums, this killer Kim Richey composition, showing she could sound pretty good when she sang something with more spunk. Too little, too late, but enjoyable nonetheless.

“You Know Me Better Than That”
George Strait
Peak: #1

Strait talks to his ex about how his new lover thinks he’s perfect, but concedes that “you know the me that gets lazy and fat, how moody I can be, all my insecurities.” While many country songs paint breakups as more final than they really are, Strait captures how the closeness of a loving relationship can cool to a knowing friendship, right down to a phone conversation where a laugh can be had at the naiveté of the new girl in the picture.

“Song of the South”
Peak: #1

A romantic portrait of the New Deal-era south, which moved a lot of farm folks into town and onto the federal payrolls. As I’ve written before, there is great irony in the anti-big government sentiments being strongest in the Republican south, which still receives more federal entitlements and benefits than any other region of the country, and by a large margin at that.

“Passenger Seat”
Peak: #12

Too often seen as a punch line rather than a legitimate country band, SHeDaisy have been putting out pop confections like this with remarkable ease. This makes you want to jump in the car, roll down the windows, and pump up the volume.

“Look At Me Now”
Bryan White
Peak: #24

White’s second single is as refreshing and sharp a decade later as it was when first released. His prodigious talent lifts this record up, and makes you wonder where the hell he disappeared to.

“Standing on the Edge of Goodbye”
John Berry
Peak: #2

Berry was the Gary Morris of the 90’s, a stocky, intense singer lacking all subtlety and nuance. His vocal growl powers the tension in this well-crafted record.

“Thinkin’ Problem”
David Ball
Peak: #2

The best way to test how much of a real country fan you are is to listen to the first three seconds of this record. If you cringe during that first “Yes, I admit”, you’re not one of us; if it piques your curiosity and you want to hear the rest of the record, you’re in the club.

“Leave Him Out of This”
Steve Wariner
Peak: #6

Something of a stepbrother to the Keith Whitley hit “Don’t Close Your Eyes”, Wariner laments that the one he’s with has someone else on her mind. His plea for her to “leave him out of this” is understated, but still powerful.

“Every River”
Brooks & Dunn
Peak: #12

One of the last acts you’d expect to cover Kim Richey, they even enlisted her to sing back-up on their recording of her declaration of lifetime love and devotion. Richey’s original surpasses the Brooks & Dunn take, but their respectable version garnered the song much-deserved exposure.

“Then What?”
Clay Walker
Peak: #2

With this out-of-left-field smash, Walker has the dubious honor of bringing Caribbean-flavored country back to the forefront. Countless years and Kenny Chesney hits later, it still hasn’t gone away. Thanks, Clay.

“As Good As I Once Was”
Toby Keith
Peak: #1
I ripped this song apart a few months ago for it’s sleazy reference to a threesome in the first verse, but the rest of it has grown on me. He actually does pull off humility surprisingly well (“I used to be hell on wheels/when I was a younger man/Now my body says ‘you can’t do that, boy’/But my pride says ‘Oh yes, you can’”). It’s a refreshing change of pace from his irritating, fake-macho swagger.

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