100 Greatest Men: #49. Toby Keith

100 Greatest Men: The Complete List

After first finding success as a smooth country balladeer, Toby Keith got in touch with his sense of humor and aggressive bravado.  The combination made him one of the biggest country stars of the new century.

One of the few acts with primarily country roots to still get radio play, Keith cut his teeth on the music of Bob Wills and Merle Haggard while growing up in Oklahoma.   Though he always made time for performing music, his first professional pursuits were in the oil fields and in semiprofessional football.

When both avenues were effectively closed for him, he pursued his music full-time, touring honky-tonks and recording demo tapes and sides for indie labels.  One of his tapes led to a deal with Mercury Records, and it contained self-written songs which would become huge hits once sent to radio.  He was a star out of the gate, reaching #1 with his first single, “Should've Been a Cowboy.”  The 1993 hit would go on to become the most played song of the nineties.

Keith became a reliable star, consistently selling gold and platinum and scoring radio hits, but he felt limited by his image as a ballad singer in the same vein as Vince Gill.   In 1999, he left Mercury for Dreamworks.   His second single for them, “How Do You Like Me Now?!” , rebranded him as a tongue-in-cheek, cocky showman, and it set the stage for him to reach superstar status.

He won the CMA trophy for Male Vocalist in 2001, but he truly hit the pinnacle of his fame the following year when he released “Courtesy of the Red, White, and Blue (The Angry American.)”   It laid the foundation for two consecutive albums selling over four million copies, and complete domination of the radio dial, with several multi-week #1 singles that became signature songs for Keith.

His massive success led to him opening up his own label, Show Dog Records, which now has a partnership with Universal Music.   Keith's record sales slowed with the new label, but overall he's doing better because of his larger financial stake in the label and the success of his restaurant chain Toby Keith's I Love This Bar and Grill.

Most recently, Clancy's Tavern became his first album in three years to earn a gold certification, and his first in six to produce three top ten radio hits.   “Red Solo Cup”, a novelty song from the set, has become Keith's biggest single in years, and as a result, exposed him to a new, younger audience.

Essential Singles:

  • Should've Been a Cowboy, 1993
  • Who's That Man, 1994
  • How Do You Like Me Now?!, 1999
  • Courtesy of the Red, White, and Blue (The Angry American), 2002
  • Beer For My Horses (with Willie Nelson), 2003
  • I Love This Bar, 2003
  • As Good as I Once Was, 2005
  • Red Solo Cup, 2011

Essential Albums:

  • Toby Keith, 1993
  • Dream Walkin', 1996
  • Pull My Chain, 2001
  • Unleashed, 2002
  • Shock'n Y'all, 2003

Next: #48. Kris Kristofferson

Previous: #50. Don Williams

100 Greatest Men: The Complete List



  1. Eh. It wasn’t one of his biggest hits (#15), and I never really thought it was one of his best either. At any rate, I don’t think it’s meant to be an exhaustive list. Wonder if there will be any flak over the inclusion of “Red Solo Cup? ;)

    My favorites are probably “Who’s That Man” and “Beer for My Horses.”

  2. I’m not really that big of a Toby fan, but like most 90’s upstarts I like his earlier material better. “Who’s That Man”, “Me Too”, “Should Have Been a Cowboy”, “You Shouldn’t Kiss Me Like This” and the 90’s sounding “Crash Here Tonight” are probably my favorite Keith songs. None of which I really love dearly though.

  3. Wow, the posts are going up like crazy at CU this week. I can barely keep up. I love it!

    One of my (few) favorite Toby Keith songs is “I’m So Happy I Can’t Stop Crying”.

  4. Toby Keith is a mixed bag for me – I really like some of his singles but some I don’t much like. I view him as primarily a singles artist in that outside of the cuts released as singles, the other album tracks strike me as being filler

    Does Toby really rank above Kenny Chesney ?

  5. I’ve always considered myself a fan of Toby Keith. The first album I ever got was Toby’s Pull My Chain. I know that it was a really controversial song at the time, for both musical and political reasons, but I still consider “Courtesy of the Red, White, and Blue” to be one of my favorites. I do agree though that after Shock’n Y’all his focus on music seems to have taken a backseat to business pursuits. And while I can’t exactly fault him for it, I’m still disappointed all the same.

  6. It’s probably not necessarily the first song everyone thinks of when talking about Mr. Keith, but “It’s A Little Too Late” is the track that stands out for me, maybe because he’s not trying to force his personality, which I have always found extremely abrasive, down the listener’s throat; there’s almost a resigned quality to it that used to be what country music was about. It also has a guitar break that reminds me a bit of George Harrison in a way.

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