​From Wikipedia, the free encyclopedia.   Toby Keith Covel (born July 8, 1961), best known as Toby Keith, was an American country music singer-songwriter, record producer and actor. 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 1990s. The song has received three million spins since then, according to Broadcast Music Incorporated. Signed to Nashville DreamWorks in 1998, Keith released his breakthrough single "How Do You Like Me Now?!" that year. This song, t...