Charlie Wilson's career dates back to the days when funk bands in Oklahoma still wore rhinestone cowboy hats. Or at least, the Gap Band -- the trio he had with his brothers Ronnie and Robert, all cousins of Bootsy Collins -- did. Their first album came out on an indie label in 1977, when Wilson was 23 years old; by the early '80s, they'd scored some of the most massively whomping funk hits in history, including "Burn Rubber on Me," "Early in the Morning" and "You Dropped a Bomb on Me," all of which Charlie sang. He also played keyboard, synth and percussion, and backed up the Eurythmics in his spare time. In the mid-'90s, he was signed as a solo act to Snoop Dogg's Doggystyle label, and in 2005, his third solo album -- Charlie, Last Name Wilson, partially produced by R. Kelly -- went Top 10 on the R&B charts and introduced him to a whole new generation; 2009's Uncle Charlie did even better. Ballads weren't really the Gap Band's specialty, but after reinventing himself as a crooner, Charlie had a handful of Top 30 R&B hits (most notably 2009's "There Goes My Baby") since the mid-'00s. He's also shown up on rap tracks by Mystikal, UGK and Kanye West.