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Phyllis Diller Crashes All-Male Roast at the Friar’s Club Dressed as a Man (1983)

Phyllis Diller dressed as a man to sneak into the Friar's Club

The Friar’s Club was founded in 1904 and, like other private social clubs of the era, their membership was male-only. Women could visit as guests but only after 4pm and the club didn’t admit its first woman as a member until Liza Minnelli in 1987.

One of the club’s biggest traditions was its closed-door luncheon roasts of celebrities, which over the years included roasts of Humphrey Bogart, Johnny Carson, Milton Berle, Redd Foxx, and Bruce Willis.1 A few women were roasted before 1987 (Lucille Ball, Martha Raye, Barbra Streisand) but they were not allowed as guests. They even sent the waiters out of the room for the roasts.

In 1983, after months of planning, Phyllis Diller dressed up as a man (named Phillip Downey) and attended the roast of Sid Caesar (she’s on the left in the photo above with her co-conspirator, Howard Rosen). Here are a pair of videos of Diller talking about her infiltration. To be fair, the Friar’s Club didn’t seem that mad at her because they roasted her just two years later.

  1. In 2004, the club roasted Donald Trump (roastmaster was Regis Philbin) and the next year Trump served as roastmaster for Don King. What a weird time/place/thing.