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Dave Chapelle in A Star Is Born

Every decade has a few movies that truly capture pop culture at that time. And while the 1990's saw countless teen movies hit theaters, few have remained quite as iconic as Clueless. Amy Heckerling's 1995 comedy is endlessly quotable, and helped make household names out of young talent like Alicia Silverstone, Paul Rudd, and Brittany Murphy. And it turns out that the cast almost included comedian Dave Chappelle.

Dave Chappelle has been steadily working as both a comedian and actor for decades, including film projects like Robin Hood: Men in Tights and A Star is Born. Clueless' director Amy Heckerling recently spoke about the iconic teen movie in honor of its 25th anniversary, where it was revealed that Chappelle nearly played the role of Murray, Dionne's boyfriend. Heckerling spoke about his inherent charm, saying:

I met people who were out there at the time and I had talked to Mel Brooks who had just done Men in Tights, and there was a guy in there that I thought was amazing, Dave Chappelle, and Mel couldn’t be more effusive and saying, he’s going to be so big, he’s amazing… I met Dave at a restaurant and he blew me away but I was looking for someone who was a totally naive puppy, and Dave Chappelle was such a mensch, not to say he isn’t a wonderful actor.

FOMO alert. It looks like Dave Chappelle was strongly considered to play Murray in Clueless, a role that would eventually go to Scrubs actor Donald Faison. Although Chappelle's natural charm turned out to be a detriment to the audition process, as Amy Heckerling was looking for a stronger sense of naivety for the character.

Donald Faison in Clueless

Later in her same conversation with The Wrap about Clueless, Amy Heckerling went on to explain how Donald Faison managed to snag the role from Dave Chappelle. Faison would also go on to reprise Murray in the Clueless TV show that followed the movie's success. As she put it,

When I met Donald Faison, he was a whippet, he just had that wonderful, energetic, innocent, fun spirit but then when he attached to read these long speeches that showed his extensive vocabulary and that he was actually really smart too, but that wasn’t the side he was pushing. It felt like he was Murray.

It's hard to imagine anyone else taking on the roles that were played to perfection in Clueless. But there were other actors considered, including the great Dave Chappelle. Unfortunately the film world is a competitive place, and the role went to Donald Faison. But both actors have had successful careers in the decades since, so it all worked out for the best.

Donald Faison was a hilarious supporting presence in Clueless, specially his arguments with Stacy Dash's Dionne. And as mentioned before, Fiason would reprise his role in the Clueless TV show for all three seasons. Of course, the actor is best most known for his iconic role as Turk in Scrubs, appearing in a whopping 179 episodes over its tenure on the air.

Clueless is currently streaming on Netflix. Be sure to check out our 2020 release list to plan your next trip to the movies.

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