Keith released his first four studio albums—1993's Toby Keith, 1994's Boomtown, 1996's Blue Moon and 1997's Dream Walkin', plus a Greatest Hits package for various divisions of Mercury Records before leaving Mercury in 1998. These albums all earned gold or higher certification, and produced several chart singles, including his debut "Should've Been a Cowboy", which topped the country charts and was the most played country song of the 1990s. The song has received three million spins since its release, according to Broadcast Music Incorporated.[2]
Signed to DreamWorks Records Nashville in 1998, Keith released his breakthrough single "How Do You Like Me Now?!" that year. This song, the title track to his 1999 album of the same name, was the Number One country song of 2000, and one of several chart-toppers during his tenure on DreamWorks Nashville. His next three albums, Pull My Chain, Unleashed, and Shock'n Y'all, produced three more Number Ones each, and all of the albums were certified multi-platinum. A second Greatest Hits package followed in 2004, and after that, he released Honkytonk University.
When DreamWorks closed in 2005, Keith founded the label Show Dog Nashville, which merged with Universal South Records to become Show Dog-Universal Music in December 2009. He has released seven studio albums through Show Dog/Show Dog-Universal: 2006's White Trash with Money, 2007's Big Dog Daddy, 2008's That Don't Make Me a Bad Guy, 2009's American Ride, 2010's Bullets in the Gun, 2011's Clancy's Tavern, 2012's Hope on the Rocks, and 2013's Drinks After Work, as well as the compilation 35 Biggest Hits in 2008. Keith also made his acting debut in 2006, starring in the film Broken Bridges and co-starred with comedian Rodney Carrington in the 2008 film Beer for My Horses.
Overall, Keith has released sixteen studio albums, two Christmas albums, and three compilation albums. He has also charted more than forty singles on the Billboard Hot Country Songs charts, including nineteen Number One hits and sixteen additional Top Ten hits. His longest-lasting Number One hits are "Beer for My Horses" (a 2003 duet with Willie Nelson) and "As Good as I Once Was" (2005), at six weeks each. He has sold more than 40 million albums worldwide.
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Toby Keith - As Good As I Once Was. Toby Keith - When Love Fades. Toby Keith - I'm Just Talkin' About Tonight. Courtesy Of The Red, White And Blue (The Angry American) Toby Keith - You Shouldn't Kiss Me Like This. Toby Keith - He Ain't Worth Missing. Toby Keith - Big Blue Note. Toby Keith - Getcha Some.
Toby Keith - Who's That Man. Toby Keith - Wish I Didn't Know Now. Toby Keith - Honkytonk U. Toby Keith - Stays In Mexico. Toby Keith - Red Solo Cup (Unedited Version) Toby Keith - Bullets In The Gun. Sundown (Live at The Fillmore New York at Irving Plaza 2010) Toby Keith - I Like Girls That Drink Beer. Toby Keith - Dream Walkin' Toby Keith - Should've Been A Cowboy. Toby Keith - Me Too. Drinks After Work (Lyric Video) HD. Toby Keith - A Little Less Talk And A Lot More Action. Toby Keith - Crash Here Tonight.
Toby Keith - I Love This Bar. Toby Keith - Get Drunk And Be Somebody. Toby Keith - Tired. Toby Keith - Made In America. Toby Keith - Beer For My Horses ft. Willie Nelson. Toby Keith - American Ride. Toby Keith - Big Ol' Truck. Toby Keith - A Little Too Late. Cryin' For Me (Wayman's Song) Toby Keith - Trailerhood. Toby Keith - I Wanna Talk About Me. Toby Keith - Hope On The Rocks. Toby Keith - Does That Blue Moon Ever Shine On You. Toby Keith - My List. Toby Keith - God Love Her. 11 Months And 29 Days (Live at The Fillmore New York at I... Toby Keith - Whiskey Girl. Toby Keith - American Soldier. Toby Keith - Who's Your Daddy? Toby Keith - High Maintenance Woman. Toby Keith - How Do You Like Me Now?! Toby Keith - Country Comes To Town.