Comedian Dave Chappelle recently recounted an awkward moment from his first encounter with the late actress Anne Bancroft, known for her iconic role in *The Graduate*. This memory surfaced during his appearance in the upcoming documentary *Mel Brooks: The 99 Year Old Man!*, which pays tribute to the illustrious career of film director Mel Brooks.
Chappelle shared his recollection of meeting Bancroft, who was married to Brooks. He described how she warmly greeted him, saying, “Oh, Mel says so many wonderful things about you.” Chappelle felt flattered by her praise but opted to lighten the mood with a joke referencing her famous character, Mrs. Robinson. He quipped, “Oh, you’re not trying to seduce me, are you, Mrs. Robinson?” This line, a nod to Bancroft’s 1967 film, elicited an unexpectedly silent response from the room.
Recognizing the misstep, Chappelle humorously reflected on the moment, noting that Bancroft had likely heard variations of that joke countless times. The atmosphere turned palpably awkward, with Chappelle recalling that the only sound was the heavy breathing of his co-star, Dom DeLuise. “That was really f—– terrible and hilarious,” he remarked, highlighting the tension of the encounter.
While the meeting with Bancroft was memorable for its discomfort, Chappelle also reminisced fondly about his interactions with Brooks. He mentioned enjoying lunch dates where Brooks would share stories, including moments when his longtime friend Carl Reiner performed their classic routine, *The 2000 Year Old Man*. Chappelle described this experience as witnessing “the greatest comedy routine by two of the greatest comics.”
The documentary *Mel Brooks: The 99 Year Old Man!* is set to premiere on HBO Max on January 22, 2026. It will celebrate Brooks’ more than seven-decade career and feature interviews with several notable figures in comedy, including Ben Stiller, Jerry Seinfeld, Nathan Lane, Judd Apatow, and Amy Schumer.
As the documentary approaches its release, Chappelle’s candid storytelling offers a glimpse into the legacy of both Brooks and Bancroft, reflecting on the personal connections that have shaped the landscape of comedy.
