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
These Country Couples Have Been Married the LongestThese country couples know the meaning of "'til death do us part."Courtney Carr
Top 10 Costumes in Country Music VideosStill don't know what you want to be for Halloween? We're here to help.The Boot Staff
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
Remember How Toby Keith Saved One of Merle Haggard’s Last Shows?He got the chance to really help his hero and friend out at the end. Sterling Whitaker
Mobster Who Swindled Toby Keith, Rascal Flatts Indicted for Fraud, Money LaunderingWhat a bizarre story.Sterling Whitaker
5 Country Singers Who’ve Never Won a GrammyKenny Chesney isn't even the most surprising singer without a Grammy Award. Billy Dukes
Top 10 Tailgating Songs in Country MusicThe Boot counts down country music's best tailgating tunes.Amy McCarthy
27 Years Ago: Toby Keith Earns His First No. 1 SongOn June 5, 1993, Keith earned his first No. 1 song on the Hot Country Songs Billboard chart, "Should've Been a Cowboy."Annie Zaleski
Toby Keith Joins Big List of 2019 CMT Awards PerformersIt's an amazing all-star lineup!Taste of Country StaffJacklyn Krol