In a recent interview, comedian Dave Chappelle recounted an awkward moment from his first encounter with the late actress Anne Bancroft. The story, shared during the promotional events for the upcoming documentary, *Mel Brooks: The 99 Year Old Man!*, highlights the challenges comedians face when humor does not resonate as intended.
Chappelle, who appears in the documentary, recalled that during their initial meeting, Bancroft warmly greeted him, saying, “Oh, Mel says so many wonderful things about you.” As she expressed her admiration, Chappelle decided to break the ice with a joke referencing Bancroft’s iconic role in the 1967 film *The Graduate*, where she portrayed the infamous Mrs. Robinson. He quipped, “Oh, you’re not trying to seduce me, are you, Mrs. Robinson?”
The comedian soon realized that this joke might have been less original than he believed. In a candid reflection, Chappelle noted the uncomfortable silence that followed his punchline, suggesting that Bancroft had likely heard the joke numerous times before. He humorously described the atmosphere in the room, stating, “The only sound was the labored breathing of my *Men in Tights* co-star, Dom DeLuise.” He added, “That was really f—– terrible and hilarious.”
Chappelle Remembers Mel Brooks
Beyond the awkward encounter, Chappelle shared fond memories of working with Mel Brooks. He recalled how Brooks would invite him to lunch and recount stories about his long-time friend, director Carl Reiner. Chappelle fondly remembered witnessing Brooks and Reiner perform their legendary routine, *The 2000 Year Old Man*, describing it as “the greatest comedy routine by two of the greatest comics.”
The documentary, *Mel Brooks: The 99 Year Old Man!*, is set to premiere on January 22, 2026, on HBO Max. This two-part special will celebrate Brooks’ remarkable career, which spans over seven decades, and will include interviews with various notable figures, including Ben Stiller, Jerry Seinfeld, Nathan Lane, Judd Apatow, and Amy Schumer.
As anticipation builds for the documentary, Chappelle’s humorous yet relatable anecdote serves as a reminder of the unpredictable nature of comedy and the enduring legacy of iconic figures like Anne Bancroft and Mel Brooks.
