Dave Chappelle Remembers Awkward Encounter with Anne Bancroft

In a candid reflection, comedian Dave Chappelle shared a humorous yet awkward encounter he had with the late actress Anne Bancroft during their first meeting. This moment is featured in the upcoming documentary, Mel Brooks: The 99 Year Old Man!, which celebrates the legendary filmmaker’s extensive career.

Chappelle’s Miscalculated Joke

Chappelle, known for his sharp wit, thought he would impress Bancroft with a joke referencing her iconic role in the 1967 film The Graduate. When Bancroft warmly greeted him, saying, “Oh, Mel says so many wonderful things about you,” Chappelle responded with, “Oh, you’re not trying to seduce me, are you, Mrs. Robinson?”

Realizing immediately that it was a line she had likely heard countless times, Chappelle recalled the silence that followed. “That was really f—– terrible and hilarious,” he remarked, reflecting on the discomfort in the room. He humorously noted that the only sound was the labored breathing of his co-star, Dom DeLuise.

Fond Memories of Mel Brooks

Beyond this awkward interaction, Chappelle expressed his admiration for Mel Brooks, who was married to Bancroft. He recounted pleasant memories with Brooks, including lunches together and witnessing the classic stand-up routine, The 2000 Year Old Man, performed by Brooks and his longtime friend Carl Reiner. Chappelle described the experience 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 HBO Max on January 22, 2026. It will feature interviews with notable figures in comedy, including Ben Stiller, Jerry Seinfeld, Nathan Lane, Judd Apatow, and Amy Schumer, highlighting Brooks’ enduring impact on the entertainment industry.

Chappelle’s recollections not only shed light on the humorous side of his interactions with the legendary actress but also emphasize the lasting legacy of Mel Brooks and his collaborators in the world of comedy.