When Phil (Wallace Langham), head writer of the titular late night program The Larry Sanders Show, leaves to write a sitcom pilot for Chappelle, he begs for his job back soon after when the then up-and-coming comedian tells him he should not write for “a black show.” The episode is meant to poke fun at a Fox pilot that Chappelle walked away from earlier that year when executives demanded more white actors. On a series known as a jumping off point for comedic talent and a fun chance at self-parody for A-listers, Dave Chappelle got to be both when he appeared as himself on Garry Shandling’s groundbreaking HBO comedy in 1998 when he was barely a household name. See if you can remember Dave Chappelle from any of these following characters, starting with one whom he already shares a name with. Granted, his characters would still often be a comic relief type, but I would still count them as the beginning of him showing his range, perhaps.Īs a tribute to one of comedy’s most celebrated living legends, we would like to celebrate a few of his roles from big screen and small screen are not considered too legendary. Yet, a dramatic role from Dave Chappelle would not be as surprising if more people knew about the movies and TV shows he was lesser-known for, which is not limited to comedies. Of course, everybody remembers his epic heckling battle in The Nutty Professor, his earlier role as Ahchoo - Bless you! - in Robin Hood: Men in Tights, his paranoia-driven hilarity in Undercover Brother, stoner favorite Half Baked (which he also wrote with Chappelle’s Show co-creator Neal Brennan), and his surprising, albeit brief, dramatic turn in 2018’s A Star is Born.
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