Toby 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 exiting 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 1990's. 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 by the RIAA. Toby Keith tickets are sold above 'face value'.

In addition to releasing his next two studio albums (2006's White Trash with Money and 2007's Big Dog Daddy, as well as the 2008 compilation 35 Biggest Hits), Keith has signed several other acts to the label, including Carter's Chord, Flynnville Train and Mica Roberts.

He has also charted more than forty singles on the Billboard Hot Country Songs charts, including eighteen Number One hits and seventeen 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 apiece.

At the age of 20, he formed the Easy Money band where he and his friends Scott Webb and Danny Smith and few other members played at local bars as he continued to work in the oil industry.

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