75. Mary Chapin Carpenter — No, I didn’t rank her ahead of the other women just because her last name is my hometown, though that didn’t hurt her any. MCC hit it big with some mid-90s songs like “I’m Feelin’ Lucky” and “Passionate Kisses.”
74. Steve Wariner — Possibly the shortest country song of all-time, I’ve always been a big fan of “Burnin’ the Roadhouse Down.” Seriously, it was like 1:59 I think. Couldn’t come up with another verse Stevie Boy?
73. Marty Stuart — Back in my lowly days of watching TNN country videos in the early 90s, I think I thought Marty and Travis Tritt were gay together. They always sang with each other and seemed so utterly happy. “High on a Mountain Top” is Marty’s best.
72. Ricochet — Hard to believe these guys are still around. Haven’t heard much from them since “Daddy’s Money.” I checked their website, and they didn’t have long hair like I remembered. Maybe I’m confusing them with Little Texas.
71. Billy Currington — I was supposed to see Billy C in concert with Jason Aldean and Trace Adkins in Mankato a couple years back, but it was winter and Billy’s tour bus went off an icy road near Chicago and he missed the show. Still like “Good Directions.”
70. Trisha Yearwood — Jordan used to be a big fan of “She’s in Love with the Boy” in the early 90s. That was a pretty good song come to think of it. Now Trisha’s in love with a boy named Garth Brooks.
69. Carrie Underwood — Carrie is really close to breaking the barrier, but she still has too many annoying songs, like “All American Girl.” I was quite the fan of hers on Idol back in the day, and even voted a few times in the early rounds, especially after 80s week.
68. Kentucky Headhunters — Only here, on this list, would the Kentucky Headhunters rank ahead of Carrie Underwood in anything. But it probably won’t be for long. I don’t know how long “Dumas Walker” and “Honky Tonk Walkin” can hold up.
67. SheDaisy — The least manliest name for a country group possibly ever, SheDaisy had a smash hit “Tonight I’m Just Me” in 2000 which might be the only country hit about schizophrenia and multiple personalities.
66. Chris Cagle — Is he gone for good, or just getting started? Chris Cagle’s “What Kinda Gone,” if I had to pick right now, would be my favorite new song in 2008. He’s a recovering alcoholic and general all-around bad boy. I think the kinda “gone” he’s talking about is the real gone. I don’t think that broad’s comin’ back for him.
65. Martina McBride — Pretty tolerable, not too annoying. These are some of the terms I’d use to describe one of country’s leading ladies, Martina McBride. And she’s been just slightly unannoying for long enough to get some real cred’ here on the list.
64. Vince Gill — Back in the 90s, women adored Vince and his boring melodramatic songs. He won CMA awards one after the other, much to my amazement and chagrin. Today things have cooled down for Vinny. One song I will remember is “What the Cowgirls Do.” He was probably referring to himself as to what the cowgirls do.
63. James Otto — Maybe the greatest palindrome-named singer of all-time, Otto has already struck big with “Just Got Started Lovin’ You.” Notice how country songs like to spell words how they say them—”lovin'” instead of “loving?”
62. Luke Bryan — All Luke’s friends say that he started shooting doubles when you walked in. Why did you do that? Why would you drive poor Luke Bryan to alcoholism!
61. Chris Ledoux — Probably the only people who think Chris Ledoux is a better country singer than Garth Brooks are the Ledoux family and Garth Brooks. I wonder if Cadillac Ranch still exists?
60. Billy Dean — Do you miss Billy the Kid or the slightly younger Billy Dean who sang that hit song about himself fifteen years ago?
59. Aaron Tippin — Mom would likely slit her wrists before listening to Aaron howling “Lookin’ for my bluuuuu—aahhhh—hoooo, ahhhh—-hoooo—-ahhhh—-hoooo angel.” But I always thought that was a good song… unless of course there was something wrong with my radio!
58. Jason Aldean — If Jason Aldean is from a Hicktown, then I must be from the town where the Hicktown sewage is pumped… or something. I don’t think Macon, Georgia, with a population of 229,000+ can be considered a hicktown!
57. Craig Morgan — Craig took a stand for farmers everywhere when he yelled at city folk to stop honking their horns as he drove his International Harvester down the highway at 3mph. He also boosted FFA sponsorships by 400% as he bellered about his sons who take part in the farming program.
56. Bon Jovi — We’re talking strictly as country artists here, so Bon Jovi isn’t quite where you’d expect. Believe it or not, when my favorite rock band turned country, I actually lost interest in them. Maybe it was because the music wasn’t very good. Hmm.
55. Rodney Atkins — If Rodney’s first album is any indication, kids could get the wrong message. He sings about his son wanting to be just like him, but also plans on holding a gun to the head of anyone who tries to date his future daughters.
54. Sammy Kershaw — Who else can sing a song about a Vidalia onion and get taken seriously? Sammy rocked the country charts in the 90s with weird songs about honky tonks in America and girls that don’t know they’re beautiful, though time and time he told them so.
53. Sara Evans — A real fine place to start with decent female artists is apparently in the early 50s. No female soloist ranks higher than Taylor or Sara! Somehow, Sara Evans slipped through the cracks and came out with some real good music, including “Suds in the Bucket,” a song Simon Cowell once scoffed at, thinking the song was about soap.
52. Taylor Swift — A difficult challenge, but males in their 20s are actually not made fun of for listening to Taylor Swift, who has defied all odds by turning in hit after hit after hit on her debut self-titled album. That’s going to be very tough to live up to when the time comes for her second album!
51. Little Big Town — Not very often you see a group mixed of males and females, and especially when all are prominent singers. LBT has gained some critical acclaim with “Boondocks” and “Bring It on Home.” I wonder what little big town they’re referring to—Huron, SD, perhaps?
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