Toby Keith’s passing at the age of 62 last night (2/5) has hit the country music community hard. The Country Music Hall of Fame said, “Toby Keith was big, brash, and never bowed down or slowed down for anyone. He wrote his breakthrough songs and later formed his own record label when he felt underserved by Nashville. For three decades, he reflected the defiant strength of the country music audience. His memory will continue to stand tall.”

In October, before his death, Keith took to Instagram to reveal that he would play two shows in Las Vegas in December. In a video clip posted to Instagram, Toby said, “Hi everybody, this is Toby Keith. It’s been a while. You know what I’ve been doing, been on the old roller coaster, but Almighty is riding shotgun. He’s letting me drive for some reason. I’m making a big announcement. I’m doing a little deal, and I would start with Great Las Vegas at the MGM at Dolby Live at the park at MGM on December 10 and 11; you can do the National Finals Rodeo and the show if you want to. I was gonna sit around here and do nothing like I have been or get up and go outside and not let the old man in, you know what I mean?” Sadly, that

He added in part, “The old devil has been after me a little bit, but I have him by the horns right now. So instead of just sitting around and waiting, we’re gonna get the band back together, so come on out, hang out at the rodeo, and watch the show. We’re gonna have a blast. Get it all going again, big dog daddy style. Should have been a cowboy; go to the rodeo. See ya.”

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Those Vegas shows, which played through January (2024), were his last shows on stage playing for fans.

Blake Shelton presented his fellow Oklahoman with the “Country Icon Award” at the September inaugural People’s Choice Country Awards (2023).

Early in his career, almost 20 years ago (2004), Blake toured and opened shows for Toby Keith nationwide. At the time, he told me, “Toby is one of those guys that is so famous and so big, and he is one of those artists that’s just worldwide. You don’t have to be a country music fan to be a Toby Keith fan. It’s just way bigger than that. I step on stage with over 20 thousand people per night, and 15,000 of them may or may not have ever heard of me. Touring with Toby has probably been the biggest break I’ve had since I started doing this.”

As the world shines a light on Toby Keith and his music today (2/6) with his passing, we shine a light on five of his greatest songs.

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"Should've Been a Cowboy" (1993)
This is his debut single and the song people will always associate with Toby. Many artists mentioned the song and its lyrics in their tribute to him after his death (2/6). Keith wrote the song himself, and it has always been his anthem. The song has received more than three million spins on country radio, making it the most-played country song of the 1990s. Over the years, the song has been a staple following sporting events at Oklahoma State University (home of the Cowboys), often played over the venue’s PA system several times in succession as fans emptied the stadium or arena.
"How Do You Like Me Now?!" (1999)
This song brought Keith to superstardom. Toby told me the inspiration for the song in 2000. “Initially, I said, ‘Here’s my title: ‘You Never Loved Me Before, So How Do You Like Me Now?’ It’s one of my catchphrases. A lot of people become successful after they’ve been told they won’t ever be so that people can relate to this. It can be about an old flame or a boss or a teacher -whatever it means to each individual. It was a fun song to write.”
"I Wanna Talk About Me" (2001)
This is another fun song and a big hit for Keith. The song was originally pitched to Blake Shelton, whose label turned it down. After recording the song, Keith said he knew he would get banged around for the song a bit. He noted, “They’re going to call it a rap, [although] there ain’t nobody doing rap who would call it a rap.”

The music video for the song shows Toby in many different situations, including a man shopping with his girlfriend or wife, a police officer, a motorcycle rider, and a surgeon.
"Courtesy of the Red, White, and Blue (The Angry American)" (2002)
The song he wrote after the 9/11 attacks on America and was also inspired by Keith’s father’s death in March 2001. In a November 2003 interview with CBS, Keith said of writing the song: “I was so angry when we were attacked here on American soil that it leaked out of me.”

The music video for the song features Toby performing the song, playing a red, white, and blue guitar, and showing images of his own father fighting in a war.
"Red Solo Cup" (2011)
Keith sure is good at fun party songs, and he proved it once again with this song, which was the only song on the album Clancy’s Tavern that he did not write. The song was written by the Warren Brothers in Nashville.

The music video includes cameos from Jeff Dunham (and his character Bubba J), Carrot Top, Ted Nugent, Sammy Hagar, Craig Ferguson, Geoff Peterson, Roger Clemens, Eric Church, Joe Nichols, Lance Burton, and Larry Bird, among others.