18. Bun B
From: Port Arthur, TX
Active Since: 1987
Career Highlights: UGK's fifth studio album Underground Kingz peaked at No. 1 on Billboard, received Grammy nominations for "Int't Players Anthem (I Choose You)" and for verse on Jay-Z's "Big Pimpin', his debut solo album Trill received gold certification and he has made countless guest appearances on major albums.
There's no questioning who's the Trill OG. Bun B has been keeping it real since he was with the deceased Pimp C as UGK. In recent years Bun B has been killing every song he's featured in: Lil Wayne's "Outro," Big K.R.I.T's "Pull Up," Killer Mike's "Big Beast." Now that's trill.