Title: Should've Been a Cowboy
Content:  "Should've Been a Cowboy" is a song written and recorded by American country music artist Toby Keith. It was released on February 8, 1993 as his debut single and the first from his self-titled debut album. On June 5, 1993, the song reached number one on the US Billboard Hot Country Songs and the Canadian RPM Country Tracks charts. It also peaked at number 93 on the Billboard Hot 100, making it a minor crossover hit. It has received more than three million spins on country radio, making it the most-played country song of the 1990s. The song is 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. American Aquarium covered the song on their 2021 album Slappers, Bangers, and Certified Twangers: Vol 1.
Title: Should've Been a Cowboy
Content:  In 2021, Adeem the Artist released the song "I Wish You Would've Been a Cowboy", an answer song to "Should've Been a Cowboy" which criticizes Keith.
Title: Should've Been a Cowboy
Content:  "Should've Been a Cowboy" debuted at number 69 on the Hot Country Songs chart for the week of March 6, 1993. It became Keith's first number one single on the chart dated June 5, 1993, remaining there for two weeks. It was certified Gold by the RIAA on November 28, 2012, almost twenty years after its release.
Title: Should've Been a Cowboy
Content:  "Should've Been a Cowboy" was Keith's first music video. It was filmed in Las Cruces, New Mexico and was directed by Marc Ball and premiered on CMT in March 1993. A second version of the video was made featuring clips of the 1992 Dallas Cowboys.
Title: Toby Keith
Content:  Keith's debut single, "Should've Been a Cowboy", went to number one on the U.S. Billboard Hot Country Songs chart in 1993, and it reached number 93 on the Billboard Hot 100. This song led off his self-titled debut album. By the end of the decade, "Should've Been a Cowboy" received more than three million spins at radio, thus making it the most-played country song of the 1990s. Certified platinum by the Recording Industry Association of America (RIAA) for shipments of one million copies, the album produced three more Top 5 hits on the country charts with "He Ain't Worth Missing" (at #5), "A Little Less 
Title: Should've Been a Cowboy
Content:  The lyrics romanticize the cowboy lifestyle through references to old Westerns. The first verse references Gunsmoke, in which cowboy hero Marshall Dillon never settled down with love interest Miss Kitty. The second verse tells of his own adventures if the narrator were a cowboy: having "a sidekick with a funny name" (possibly a reference to sidekicks like Tonto or Gordito), travelling west to California (including the historical quote "Go West, young man"), hunting down Western outlaw Jesse James, joining up with the Texas Rangers, and so on. The chorus refers to famous singing cowboys Gene Autry and Roy Rogers, and lists common patterns depicted in Westerns such as six-shooters (revolvers) and cattle drives.
Title: Toby Keith (album)
Content:  Toby Keith (known as Should’ve Been a Cowboy on the 2018 re-release) is the debut studio album from American country music artist Toby Keith. Released in 1993 on Polygram Records, it features the singles "Should've Been a Cowboy", "He Ain't Worth Missing", "A Little Less Talk and a Lot More Action", and "Wish I Didn't Know Now". Respectively, these songs peaked at No. 1, No. 5, No. 2, and No. 2 on the Hot Country Songs charts. The album sold more than one million copies in the United States, earning RIAA platinum certification. All the songs except for Some Kinda Good Kinda Hold On Me and A Little Less Talk And A Lot More Action were written by Toby Keith. "A Little Less Talk and a Lot More Action" was previously recorded by Hank Williams, Jr. on his album Maverick (1992). A remastered 25th anniversary edition, retitled Should’ve Been a Cowboy as a nod to the hit single from the album, was released on November 30, 2018 with three bonus tracks added.
Title: Cowboy (Kid Rock song)
Content:  "Cowboy" is a song by Kid Rock from his album Devil Without a Cause. The song, noted for its country rap style, reflects a cross-section of Kid Rock's country, Southern rock and hip hop influences, having been described by the artist as a cross between Run DMC and Lynyrd Skynyrd. "Cowboy" was Kid Rock's first single to chart on the Billboard Hot 100, peaking at number 82, while reaching number 10 on the Mainstream Rock charts. With its lyrics about pimping and traveling to California, the song is considered to be one of Kid Rock's best works, and has been claimed as greatly influencing modern country music   and as the first country rap song.
Title: A Cowboy Has to Sing
Content:  A Cowboy Has to Sing is the third Sons of the San Joaquin album and the first for a major label. All of the album's songs were written by members of the Sons of the Pioneers. Though newly recorded, the songs on this album can all be found on the two previous releases.
Title: Cowboy (Kid Rock song)
Content:  In 2002, the music group Boys Don't Cry filed suit against Kid Rock, claiming the song "Cowboy" was derivative of their 1986 synth-pop track "I Wanna Be a Cowboy", and alleged that Kid Rock, while DJing in Detroit, had played the song; the suit claimed that Kid Rock had taken the bassline and adapted his chorus from the 1986 song.

Question: who sang the song should have been a cowboy?
Answer: Toby Keith.