Five of Toby Keith's Songs That Will Live Forever

• "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.