Jon Stewart’s Greatest Lesbian Moments


Lily Tomlin (June 8, 2006)

Both funny and classy — a combination that’s almost extinct — Lily Tomlin stopped by to talk about making Garrison Keillor’s A Prairie Home Companion with Robert Altman, Meryl Streep and Lindsay Lohan. When Stewart confided that he was a little worried about Lohan, Taylor reported that Streep, who has two daughters of her own, was too. "I personally wanted to go out to the clubs with her," Taylor confessed.

(or watch the video here)

Cynthia Nixon (July 29, 2002)

When Cynthia Nixon stopped by to talk about Sex and the City in 2002, it was two years before she came out, which makes the subtext of Stewart’s first words to her all the more striking. Referring to the screams and catcalls from the audience, he said, "You’re like a boy band for ladies." Exactly.

(or watch the video here)

Angelina Jolie (April 21, 1999)

Angelina Jolie’s been on The Daily Show four times, but hands down, her 1999 guest appearance — dressed in black leather pants and dykey boots, no less — was her best. She even admitted that her first crush was Star Trek‘s Mr. Spock, saying, "He was so repressed, you just wanted to make him scream." When Stewart asked if her newfound celebrity felt like running a gauntlet and getting paddled, she just looked up from under her lashes and purred, "I don’t mind paddles."

Stewart briefly lost his ability to speak. You will too.

(or watch the video here)

If what you like is a more glamorized Angelina, don’t miss her other three appearances, including a July 2003 gigglefest, an October 2003 visit where she discusses her role in Alexander and working for the U.N., and a June 2007 interview in which there’s a little flirting, a little politics, and a little joking about her hotness. It’s actually a great interview for Jolie, but not Stewart’s finest hour. It seems her hotness got to him.

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