28 Years Ago: Toby Keith Releases His Debut Single, ‘Should’ve Been a Cowboy’In February of 1993, Keith released his debut single, "Should've Been a Cowboy."Annie Zaleski
Toby Keith Visibly Moved by Tender Acoustic Cover of His Best Love Song [Watch]Singer Darbi Shaun covered Keith's 1999 hit "You Shouldn't Kiss Me Like This" on TikTok, and the star found it for one of his duets.Billy Dukes
Toby Keith, Ricky Skaggs Honored by Donald Trump Amid Impeachment ProceedingsA representative for Keith has declined comment.Billy Dukes
16 Years Ago: Toby Keith’s ‘Shock’n Y’all’ Becomes His Second Quadruple-Platinum AlbumOn Oct. 21, 2004, Keith undoubtedly raised a glass or two in celebration.Gayle Thompson
Terrible Movies Starring Country ArtistsThere are many things that country artists are good at -- but these movies are not among them.Riane Konc
26 Years Ago: Toby Keith Hits No. 1 With ‘Who’s That Man’On Oct. 8, 1994, Keith was undoubtedly raising a glass to toast to his success.The Boot Staff
These Country Couples Have Been Married the LongestThese country couples know the meaning of "'til death do us part."Courtney Carr
Hut, Hut, Hike! Country Stars Who Have Played Football [PICTURES]Some of country music's biggest names got out on the gridiron before they made it big in music.Hannahlee Allers
18 Years Ago: Toby Keith Hits No. 1 With ‘Courtesy of the Red, White and Blue’On July 20, 2002, Keith earned his ninth No. 1 single with his tune "Courtesy of the Red, White and Blue (The Angry American)."Gayle Thompson
Top 10 Toby Keith SongsKeith's songs are some of the most popular of the last few decades in country music.The Boot Staff