Both are multiple Grammy winners for best comedy album. Carlin won five times—second only to Bill Cosby (who won seven wins in that category). Chappelle has won the last three years running. Carlin received 16 nominations in the category, more than anyone else in history. In addition, his 1972 album Class Clown was voted into the Grammy Hall of Fame in 2010.
Both received Emmy love (though not enough, in Carlin’s case). Carlin received six nominations, including three nods for outstanding variety, music or comedy special. Unfortunately, he never won. Chappelle has received seven nominations, including two wins – most recently for outstanding variety special (pre-recorded) for Dave Chappelle: Equanimity (2018).
Both starred in their own TV series. Carlin headlined The George Carlin Show on Fox in 1994-95. Chappelle starred in Chappelle’s Show on Comedy Central from 2003-06.
Both also acted in straight dramatic roles in films -- including in films that were Oscar-nominated for best picture. Chappelle had a role in the 2018 remake of A Star Is Born, directed by Bradley Cooper. Carlin had a role in 1991’s The Prince of Tides, directed by Barbra Streisand. Carlin’s other films include Car Wash (1976), Bill & Ted’s Excellent Adventure (1989) and Jersey Girl (2004). Chappelle’s other film roles include The Nutty Professor (1996), Con Air (1997) and You’ve Got Mail (1998).
Both headlined numerous stand-up specials. Carlin starred in 14 such specials, all for HBO, from 1977-2008. Chappelle has headlined eight since 2000.
Both have hosted NBC’s Saturday Night Live. Carlin hosted the very first episode back in October 1975. Chappelle hosted a 2016 episode. That appearance brought Chappelle his first Emmy, for outstanding guest actor in a comedy series (2017).