Everybody remembers Dave Chapelle’s epic heckling battle in The Nutty Professor, his earlier role as Ahchoo – Bless you! – in Robin Hood: Men in Tights, his paranoia-driven humorous character in Undercover Brother, stoner favorite, and his surprising, albeit brief, dramatic turn in 2018’s A Star is Born. As a tribute to one of comedy’s most celebrated living legends, we would like to celebrate a few of his roles that are generally not considered too legendary and are often forgotten about.
Dave (Home Improvement)
Tim (Tim Allen) gets a crash course in how not to talk to women by giving a pair of Tool Time audience members’ bad romantic advice. The two gentlemen are Dave Chappelle as “Dave” and Jim Breuer as “Jim” in this 1995 Home Improvement episode that would earn the real-life friends their own sitcom called Buddies… until Breuer was fired days before the intended premiere. The series was cancelled after five episodes and, thankfully, Breuer and Chappelle would later co-star in Half Baked.
Pinball Parker (Con Air)
A year before said iconic 1998 stoner comedy, Dave Chappelle starred in something a little more unlikely: the enjoyably ridiculous Jerry Bruckheimer-produced action flick Con Air. Of course, in retrospect, his character, Pinball Parker, is easily the funniest passenger on the hijacked prison transport plane that Cameron Poe (Nicolas Cage) is desperate to flee so he can see his daughter. Hell, even Chappelle’s death scene (followed soon after by his corpse free falling to the A Summer Place theme) is clearly played for laughs.
Rusty P. Hayes (Screwed)
Dave Chappelle’s role was bigger, but his crime was smaller and probably far more problematic for himself, in the 2000 comedy Screwed. He plays Rusty P. Hayes, whose friend (Norm Macdonald) seeks revenge on his wealthy, vile boss (the late Elaine Stritch) by kidnapping her dog, until they have to think of a new ransom idea when she accidentally gets it back. This slapstick comedy (also starring Danny DeVito as a gross mortician) cost about $10 million to make and made a little over $7 million worldwide, which is probably why you might not have heard of it.
Cockroach (Joe’s Apartment)
You more likely have heard about this gross out comedy, the first produced by MTV Films, about a young guy (Jerry O’Connell) who moves into a New York apartment overrun with talking, singing cockroaches. What you may not have realized is that Dave Chappelle provided the voice of one of the many CGI pests (who look pretty good for a 1996 flick) in Joe’s Apartment. However, unlike Billy West’s Ralph Roach or Reginald Hudlin as Rodney, Chappelle’s roach was never given a name.
Kevin Jackson (You’ve Got Mail)
Dave Chappelle got to show his face and play opposite the one and only Tom Hanks as Kevin Jackson in You’ve Got Mail. In addition to playing the friend and co-worker of Hanks’ corporate bookstore owner, he also gets to be the one to break it to him that the woman he has been falling in love with over the Internet in his business rival, a local bookstore owner (Meg Ryan) who despises him in person as equally as he does her. It is crazy to me how this classic Nora Ephron rom-com from 1998 is probably one of the biggest films of Chappelle’s career and his presence in it is rarely (if not ever) acknowledged.
Disco Cabbie (200 Cigarettes)
Well, at least Dave Chappelle is not alone in that regard when it comes to this underrated 1999 dramedy that often goes unmentioned when discussing the filmographies of its entire star-studded ensemble, including Ben Affleck, Christina Ricci, Paul Rudd, Kate Hudson, Courtney Love (yes, that Courtney Love), and Elvis Costello as himself. Chappelle’s role, known only as Disco Cabbie for his decked, funky taxi, is the one character whom most of the cast of romantically challenged New Yorkers have in common during a fateful New Year’s Eve in 1981.
Spike Lee reinterprets the Greek morality play Lysistrata as a satire on the connection between violence and sex set in modern-day Chicago, or “Chi-Raq” – the real-life nickname the Illinois city earned by its crime rate. The story focuses on a group of women, led by WandaVision’s Teyonah Parris, who fight violence with chastity, which causes problems for business in a local night club owned by Dave Chappelle’s Morris, who lectures his best customers over how the fatal consequences of their actions has led his strippers to quit in protest.
Dave Chappelle (The Larry Sanders Show)
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. 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.