In a recent appearance in the upcoming documentary Mel Brooks: The 99 Year Old Man!, comedian Dave Chappelle recounted an uncomfortable moment from his first meeting with actress Anne Bancroft, who was married to legendary filmmaker Mel Brooks. Chappelle shared a joke referencing Bancroft’s iconic role in the 1967 film The Graduate, but the punchline fell flat, leading to an awkward silence.
Chappelle’s Joke and Its Consequences
During the documentary, Chappelle recalled that Bancroft greeted him warmly, saying, “Oh, Mel says so many wonderful things about you.” Feeling playful, Chappelle responded with, “Oh, you’re not trying to seduce me, are you, Mrs. Robinson?” The joke, a nod to Bancroft’s character in The Graduate, did not elicit the laughter he expected.
Realizing that Bancroft had likely heard variations of that joke countless times, Chappelle noted the immediate silence that followed. He humorously remarked that the only sound breaking the quiet was the strained breathing of his co-star, Dom DeLuise. “That was really f—– terrible and hilarious,” Chappelle reflected on the moment.
Memories of Mel Brooks and the Upcoming Documentary
In addition to the anecdote about Bancroft, Chappelle shared fond memories of his time with Mel Brooks. He described moments when Brooks would take him to lunch, and they would encounter their mutual friend, director Carl Reiner, who was working on a film nearby. Chappelle cited a performance of Brooks and Reiner’s classic routine, The 2000 Year Old Man, as “the greatest comedy routine by two of the greatest comics.”
Mel Brooks: The 99 Year Old Man! is a two-part documentary set to premiere on HBO Max on January 22, 2026. The film celebrates Brooks’ remarkable career, which spans over seven decades and features interviews with notable figures such as Ben Stiller, Jerry Seinfeld, Nathan Lane, Judd Apatow, and Amy Schumer.
This documentary not only highlights Brooks’ influential work in comedy and film but also provides a glimpse into the personal experiences of those who admired him, including Chappelle. As the world awaits its release, moments like Chappelle’s encounter with Bancroft remind us of the complexities of humor and the connections formed through shared laughter.
