On his journey to the top of the comedy heap, Dave Chappelle missed out on a few movie roles that would’ve been career-defining for other up-and-coming actors. One such opportunity came in the early ‘90s, when he was sent the script for Forrest Gump. Chappelle said he turned down the part of Benjamin Buford “Bubba” Blue because he didn’t think it was a good fit for him. The comedian also apparently auditioned for Rush Hour, which obviously didn’t work out in his favor.
For the 25th anniversary of Clueless in 2020, the film’s writer and director, Amy Heckerling, sat down for a Q&A with TheWrap, where she revealed that Chappelle was in the running for the role of Murray as well. According to Heckerling, she’d heard of Chappelle through Mel Brooks, who had nothing but nice things to say about working with the fledgling comic on 1993’s Robin Hood: Men in Tights. Evidently, Brooks saw that Chappelle had great potential and told Heckerling that he was destined for success.
Heckerling agreed, and recalled thinking Chappelle was “amazing,” just not for the part she was looking to cast back then.
Dave Chappelle Almost Starred in ‘Clueless,’ but the Director Thought He Was Too Smart for the Role
Heckerling met with Chappelle at a restaurant to discuss the potential gig, and was blown away during that initial meeting. She went on to describe Chappelle as a “mensch,” which was precisely the problem she had with hiring him. Heckerling went on to explain that she wanted the Murray character to be innocent and goofy. Despite acknowledging Chappelle’s “wonderful” acting ability, he unfortunately lacked the naïveté to pull off the role.
Donald Faison, in contrast, had all the qualities Heckerling was seeking, and wound up playing Murray in the end. “When I met Donald Faison, he was a whippet; he just had that wonderful, energetic, innocent, fun spirit,” Heckerling remembered, “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,” she continued.
“It felt like he was Murray.”
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