Toby Keith, 61, is nothing short of a country music legend. From his eponymous debut album in 1993 to his efforts as a music producer and beyond, he’s been a household name for decades. The Arkansas native boasts an impressive array of awards over his career, including CMA Male Vocalist of the Year (2001), Academy Of Country Music’s Entertainer of the Year (2002-2003,) and American Music Award’s Favorite Country Male Artist (2004 & 2006.)

He dipped his toe into the movie industry with starring roles in 2005’s Broken Bridges and 2008’s Beer for My Horses, which he also wrote. As an entrepreneur, his enterprises include a chain of restaurants called Toby Keith’s I Love This Bar & Grill, a line of clothing called TK Steelman, and a drink called “Wild Shot.” All of these efforts, including his own record label, Show Dog-Universal, have helped make him one of the wealthiest celebrities in the country.

Toby has also courted political controversy, facing off with the Dixie Chicks over his conservative anthem “Courtesy of the Red, White, & Blue” and backing up former President Donald Trump by performing at