In Memoriam: Toby Keith (1961-2024)

Country music legend Toby Keith has passed away at the age of 62, following a battle with stomach cancer.

Variety reports:

Born in Clinton, Okla. on July 8, 1961, Keith started his career in music at the age of 20 by forming the Easy Money Band with his friends. In the mid-’80s, the group began playing at honky-tonks in Oklahoma and Texas, and by the ’90s Keith was husking in Nashville in hopes of getting a record deal. His big break finally came when a flight attendant gave his demo tape to Mercury Records exec Harold Shedd, who had worked with Shania Twain and Billy Ray Cyrus. Shedd signed Keith and released his 1993 debut single, “Should’ve Been a Cowboy,” which reached No. 1 on Billboard’s country songs chart. The song would go on to become the most-played country song of the decade.

In 1999, Keith moved to DreamWorks Records. His first single on the label, “When Love Fades,” performed poorly on the charts so he had it withdrawn and replaced by “How Do You Like Me Now?,” which became his first song to break through the top 40 on the Hot 100, peaking at No. 31. The album “How Do You Like Me Now?” was released later that year and produced another country No. 1 with “You Shouldn’t Kiss Me Like This.” His 2001 album “Pull My Chain” followed a similar trajectory, with all three singles — “I’m Just Talkin’ About Tonight,” “I Wanna Talk About Me” and “My List” reaching the top spot on the country charts.

Keith’s rapid-fire success slowed a little after DreamWorks ceased operations and he started his own label, Slow Dog Nashville. His 2006 album, “White Trash With Money,” didn’t make as big of a splash, but 2007’s “Big Dog Daddy” saw his first No. 1 since 2005 with “Love Me if You Can.” “Big Dog Daddy” was followed by another Christmas album and greatest hits compilation, and two more hits-producing albums, 2008’s “That Don’t Make Me a Bad Guy” and 2009’s “American Ride.”

2010’s “Bullets in the Gun” was Keith’s first record that didn’t result in a top 10 hit. But Keith couldn’t dodge success for too long — 2011’s “Clancy’s Tavern” contained the No. 1 song “Made in America” and “Red Solo Cup,” Keith’s biggest crossover to date which peaked at No. 15 on the Hot 100.

We’ve been writing about Toby Keith for as long as Country Universe has been around, and as one of the most important legacy acts of the nineties, his death hits us particularly hard.

Watching Keith go from genuinely underrated in the nineties into a genre-defining superstar in the 2000s, one thing that remained consistent was his top notch songwriting and incredibly strong vocal performances.

Keith may have been the last male country superstar that was fully tethered to the genre’s roots, with a clear line connecting him back to Haggard, Jones, and Whitley. Even as he aged out of country radio, he continued be to produce great songs, so much so that most of my most played tracks of his (“A Little Too Late,” “In a Couple of Days,” “Drunk Americans”) came along after his mulitplatinum peak in the early-to-mid 2000s.

It feels especially tragic that Keith won’t be around for his inevitable and well-deserved induction into the Country Music Hall of Fame, which is the most damning indictment yet for the ridiculous bottlenecking going on in that institution.  An artist of Keith’s caliber should’ve been in there by the end of his fifties at the very latest.

Our deepest condolences to Keith’s family, friends, and fans.

Please share your favorite Keith song in the comments, and I’ll add them to the Spotify and YouTube playlists. I’ve started things off with my favorite: “In a Couple of Days.”- KJC

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  1. I was in fifth grade when “How Do You Like Me Now” was released and it’s the first album I can remember buying based on one song only to find I liked a lot of the album cuts more than the singles. For those who only know his radio material it’s definitely worth digging into the album tracks, especially on his earlier work.

  2. Such sad news to start the day.

    Though I appreciate he’s had many more substantial hits than this one, my personal favorite song by Toby Keith is “I Love This Bar.” Inclusive. Infectious. And fun!

  3. Wish I didn’t Know Now. Very clever turn of phrase and Toby sings the hell out of it. I always thought it sounded like a track that was made for Dwight Yoakam.

  4. I think you guys did a great job highlighting TK on your 90’s country feature. I go back to it all the time. Really helps spotlight how underrated Toby was in the 90’s. If you listen to Toby’s 90’s songs he had very unique production choices that are really moody. “Who’s That Man” is what I would point to or “He Ain’t Worth Missing”.

  5. Toby was a real Jekyll and Hyde between his singles and his album tracks. The former led to his jingoistic (and profitable) brand, but the album tracks had way more sensitivity and self awareness. He was a genuinely brilliant songwriter, and I hope that’s some of his legacy. Some of my favorites are:

    You Leave Me Weak:

    Losing My Touch:

    I Won’t Let You Down:

    Where You Gonna Go:

    And finally his cover of White Rose is excellent:

  6. Pretty heartbroken over this.

    It may be the fan boy in me but Toby wrote and recorded a unique style of country music that stood out so much during a very great time in country music.

    He was a voice for so many country fans, always being supportive of our troops and their families. He was a great singer, writer, patriot, Christian, human being, and role model. Here’s hoping he is inducted into the Country Music Hall of Fame very soon.

  7. Toby Keith’s catalogue is one I need to explore deeper, but I really enjoyed a lot of his output. My List might be one of my favorite “list” songs in country music and a mentality I try to live by. Rest in peace to a country legend.

    • Your contributions have been amazing. I’ve discovered so many new songs already!

      We’ve never done this on an IM thread before, but I love it is a way to collectively grieve a death and celebrate a life’s work.

      • I’ve found a bunch of new songs too thanks to this thread. This was a great idea, it’s nice how an artist that was around for damn near 40 years can still surprise you.

  8. We Were In Love is my favorite. I specifically love how Toby and the production ramp up in intensity all throughout the the bridge and chorus only for his voice to crack and mournfully soften when he reaches the line “and we were in love”. It’s the perfect example of Toby Keith’s greatest strength as an artist. Toby’s vocals masterfully meshed with the lyrics and tone. It’s a hard idea to convey in writing. Give it a listen.

    RIP to a modern country classic artist.

  9. Thanks for all the thoughtful writing about Toby over the years, and thanks for putting together this playlist! I was just reading through some of the old posts a few months ago. I had the privilege of seeing Toby at a free county fair show in 1998 shortly before he reached superstar status. It’s hard to believe that some of the 90’s country artists I saw back then like Toby, Joe Diffie, and Doug Supernaw are already gone.

    I can’t claim to know his album cuts very well, although I’m enjoying listening to them today. Out of his singles, I’d probably pick “He Ain’t Worth Missing” as my favorite. Honorable mention to “I’m So Happy I Can’t Stop Crying”, “Wish I Didn’t Know Now”, “My List”, “Does That Blue Moon Ever Shine On You”, “Should’ve Been A Cowboy” (duh), …

  10. …i always had a soft spot for his “heart to heart” (selen’s song) and for “crying for him” (wayman’s song) his heartfelt tribute to wayman tisdale. and somwhat against my will and reason, i enjoy “courtesy of the red, white and blue”. probably a lot more than the huthis do these days. timeless songs. not to mention so many of his others. what a character and artist he was.

  11. I was a Toby Keith apologist with many of my friends and neighbours right up to his 2021 “Peso in my Pocket” album. His brand and blunt personality made him easy to dismiss until you bothered to listen to his albums, and as has been made abundantly clear throughout these shares and comments, he was an artist of significance.

    I will miss him.

    I picked my favourite track from each of his cds still sitting on my shelf.

    “Momma Come Quick” from “Toby Keith.

    “Upstairs Downtown” from “BoomTown”

    “Tired” from “Dream Walkin'” is when I first realized just how good his writing was .

    “I’m Just Talkin’ About Tonight” from “Pull My Chain” captures his fun-loving spirit and sense of humour as well as anything else he recorded.

    “Huckleberry” from “Unleashed.”

    “Don’t Leave, I Think I Love You” from “Shock’n Y’All”

    “Knock Yourself Out” from “Honkytonk University”

    “A Little Too Late” from “White Trash with Money”

    “Walk it Off” from “Big Dog Daddy”

    “Hurt a Lot Worse When You Go” from “That Don’t Make Me a Bad Guy”

    “In a Couple of Days” from “Bullets in the Gun”

    “You Aint’ Alone” from “Hope on the Rocks”

    “Just Another Sundown” from “Clancy’ Tavern”

    “Beautiful Stanger” from “35 mph Town”

    “Growing Up is a Bitch” from “Peso in my Pocket”

    Thank you, to the readers and commenters, for this country music community.

  12. Thanks for the additional suggestions! I’ve updated both lists and added two more favorites of mine – “Getcha Some” and “I Like Girls That Drink Beer” – to make it an even forty tracks.

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