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Jon Stewart’s Greatest Lesbian Moments

Since taking over as host of Comedy Central’s Daily Show in 1999, Jon Stewart has made “fake news” a part of the cultural vernacular. He has demonstrated that there’s a market for smart, political commentary – as long as it also makes people laugh. And he has shown that being really angry can also be really funny.

Fortunately for us, one of the things that makes him angriest – and funniest – is injustice against the queer community.

And unlike many men on the left, whether they’re comedians or pundits, Stewart has never made lesbians and bisexual women an afterthought in either his outrage or his humor. He consistently uses real-life lesbians as examples when discussing general LGBT political issues, and lesbian images appear as often as those of gay men, if not more frequently.

In October 2007, the show launched a vast archive of video clips at TheDailyShow.com, and now that the WGA strike seems to have no end in sight, there’s no better time to work your way through the funniest queer moments of Stewart’s eight-year tenure as the nation’s leading fake newsman. We’ve already reviewed some of his greatest gay moments on AfterElton.com, and now we take a look at some of his best lesbian ones. (A word of warning: The web archive still has the word “beta” appended to its logo, and there are still a few clips that don’t always work properly.) When it comes to fodder for scathing political comedy, lesbians aren’t the first group that comes to mind. That’s because powerful, closeted lesbian conservatives rarely get arrested in public restrooms or are exposed as prostitute-soliciting, meth-using televangelists. No, that ground definitely belongs to the guys.

So where did all that lesbian material come from? A big hunk of it comes from one of the longest-running displays of political hypocrisy in the history of American government, Mary Cheney.

Mary Cheney is, of course, the out lesbian daughter of Vice President Dick Cheney, or as Stewart describes him: “Dick Cheney: Conservative. Draconian. Drinks the blood of puppies.”

So just what bugs Jon Stewart about the vice president and his daughter? Maybe it’s the way he claims to love her and support her while his political party devotes vast amounts of energy to making sure she never gets better than second-class citizenship. Or the way questions about the Republican Party’s policies on LGBT issues are somehow an invasion of Cheney’s family’s privacy – even though Mary Cheney is out, lives with her partner, and wrote a book about being the out lesbian daughter of the vice president.

Lesbian political content on The Daily Show doesn’t end with Mary Cheney, however. From same-sex marriage to right-wing values pundits like William Bennett and Dr. Laura, there’s a whole lot of lesbian gold to be mined in the Daily Show‘s brand new clip archive.

Protesting Dr. Laura (March 15, 2000)

Making fun of conservative radio personality Dr. Laura is kind of like shooting fish in a barrel. She does all the work for you, really.

Here, she’s even more upset over If Walls Could Talk 2 than she was over Heather Has Two Mommies. This segment includes a beautiful clip of a lesbian wedding (which was also that night’s Moment of Zen). Dr. Laura also sarcastically apologizes to her listeners for not being Sharon Stone or Ellen DeGeneres. And well she should.

Bill O’Reilly Fails to Predict the Future (March 14, 2002)

Jon’s feeling our pain in this one, no question about it. In the second part of an interview with Fox News pundit Bill O’Reilly, Stewart lets O’Reilly explain why the only responsible thing queer people can do is stay in the closet. Take Rosie O’Donnell, who had just come out that week in an interview with Diane Sawyer. Who wants to hear about her private life? Not O’Reilly, that’s for sure.

Or take Ellen DeGeneres. “Very funny, very smart,” O’Reilly began. “She will never succeed on television because a large part of America does not want to hear about her sex life.” That was before The Ellen DeGeneres Show won four Emmy Awards, including Best Talk Show, in its first season alone, and went on to become one of the most popular daytime shows in TV history, averaging 3 million viewers a day. (O’Reilly’s show, which is losing viewers every year, currently clocks in at 2 million.) “Queers Vie for the Straight Tie” (Feb. 23, 2004)

A perfect example of how Stewart gives lesbians parity with gay men in stories about LGBT issues is a clip about same-sex marriage illustrated entirely with lesbian weddings, including the wedding of California state Sen. Carole Migden and attorney Cristina Arguedas, which San Francisco Mayor Gavin Newsom officiated. The two women had been partners for more than 20 years when they finally tied the knot. “The Ring” (Feb. 26, 2004)

Jon gives lesbians better than parity yet again in another feature about gay marriage that includes an all-lesbian news montage. The segment wraps up with film of Rosie O’Donnell’s San Francisco wedding to longtime partner Kelli Carpenter, as well as a clip of her on Good Morning America telling Diane Sawyer what she thinks of a constitutional amendment to ban gay marriage. Lesbian visibility doesn’t get much better than that, especially when there’s absolutely nothing titillating going on.

“Queer and Present Danger” (March 23, 2004)

Daily Show correspondent Ed Helms does what he does best: Turns the words and prejudices of right-wing homophobes against them by adopting their attitudes as his own. In this series of interviews held in San Francisco in the days following Mayor Newsom’s issuance of same-sex marriage licenses, Helms introduces viewers to a recently wed lesbian couple as well as two straight couples he characterizes as “victims of gay marriage.” (It should be noted that neither of those couples said that about themselves.)

The whole segment is hysterically funny, and the three couples are perfectly chosen. The cherry on the top? When Helms leeringly asks the two lesbians about their wedding night activities, one of the brides gently informs him that being a lesbian means never having to say yes to a three-way with an obnoxious anchorman. “This Week in God: Deity Contraption” (March 9, 2005)

This one’s a lesbian double-header from Stephen Colbert in his Daily Show days: beginning at 3:18, the Anglican Church’s schism over same-sex marriage, followed by some Sapphic sorority house true confessions. It’s like a spiritual experience – but funny. Jon Stewarts Takes Down Bill Bennett (June 6, 2006)

This is Stewart at his pure gold best, relentlessly hammering right-wing values guru William Bennett on the fundamental unfairness and mean-spiritedness of denying same-sex couples the right to marry.

A great deal of this interview’s power comes from the obvious pain and anger Stewart feels at Bennett’s unwillingness to concede that, just as Dick Cheney opposes a constitutional amendment banning gay marriage because of his support for his lesbian daughter, the reality is that every lesbian and gay man is someone’s child. No one does angry better than Stewart.

And seeing William Bennett get his butt kicked is always a plus.

Stewart Calls Out Dick Cheney (Jan. 25, 2007)

Since his 2004 interview with Bill O’Reilly, Stewart has clearly gotten a lot more pissed off about the inherent injustice of denying lesbians and gay men marriage equality. Commenting on a Wolf Blitzer interview with Dick Cheney, Stewart asks in a pretty terrible imitation of Cheney, “How dare you apply my party’s cruel and inhumane family policies to my family?”

Then he asks: “Hey, Mr. Vice President! Aren’t any other gay people somebody’s kid?” Good question. (Hint: Darth Vader’s daughter is also a dyke.) There’s Something About Mary (Feb. 1, 2007)

In an episode that probably should have been titled “All Mary Cheney, All the Time,” Stewart went looking for hypocrisy and found it everywhere. First was a painfully awkward clip of Wolf Blitzer asking the vice president about his daughter’s pregnancy.

Stewart then contrasted a clip of Cheney thanking vice presidential contender John Edwards for his “kind words” about Mary, with another showing him blasting fellow candidate John Kerry for doing exactly the same thing in the presidential debate. The commentary continues with an examination of how questions about LGBT civil rights are actually an invasion of the Cheney family’s private life. Daily Show “senior media critic” John Oliver then explains it in terms even Cheney’s new baby grandson and his two mommies can understand: Stewart wrapped up the Mary Cheney show by bringing in another daughter of a prominent Washington politician, former Rep. Richard Gephardt’s lesbian daughter, Chrissy Gephardt.

Like Mary, she’s out and an articulate spokesperson for her party and her views. Unlike Mary, she’s got a wicked sense of humor, particularly when responding to Stewart’s concerned probing about “the incredible damage done to children raised by politicians.”

“Indecision v.2.008”: John McCain Hacked (March 29, 2007)

This segment is what “fake news” is all about. First, the real news, starting at 2:32 – a report that Sen. John McCain’s MySpace page was hacked and a note was added to his campaign FAQ stating that he now supports same-sex marriage, “particularly marriage between passionate females.”

Then the fake news: the campaign’s response. Jon Stewart is famous for giving even controversial guests a fairly easy time with their interviews, which may be why so many conservative commentators, politicians and writers have been guests on his show.

Whether that’s good or bad when it comes to political guests is an open question, but for celebrity guests, it’s pretty much a blessing. Almost everyone is eager to sit down with Stewart, knowing they can spend their 10 minutes cracking a few jokes and not having to fear the slings and arrows of outrageous journalism – including some of television’s best-known lesbians and bisexual women.

Ellen DeGeneres (March 2, 2000)

When DeGeneres visited The Daily Show to promote If Walls Could Talk 2, the interview turned into a love-fest between two of the funniest people on television. She stopped playing with her swag basket long enough to tell Stewart: “I love you. I absolutely love you. And I think I speak for all lesbians. Because I’m the leader of all lesbians, as you know.” Jodie Foster (Sept. 11, 2007)

Earlier this year, Jodie Foster was on the promo trail for her film The Brave One when the famously publicity-shy star made a stop at Stewart’s desk. She looked great; two women screamed “We love you, Jodie!” at the top of their lungs; and audience enthusiasm was the theme of the evening.

Unfortunately, the Daily Show clip archive is currently earning its “beta” label with some clips suddenly becoming unviewable, and Foster’s is one of them. Desperate fans can just keep clicking the “Jodie Foster” tag until it works again.

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. 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. 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. 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.

Margaret Cho (June 28, 1999)

Queer icon Margaret Cho had Stewart on the run from the minute she sat down. They bonded briefly over a mutual love of dogs, but the truth is, she was just funnier than he was. When an actress stops by any talk show to promote a recent film or TV show in which she plays a lesbian, the host almost always makes stereotypical jokes about “researching” lesbianism. Stewart is no exception, but he has also managed to restrain himself.

Jennifer Beals (March 29, 2004)

In her second appearance on the Daily Show, Jennifer Beals was promoting The L Word, then in its first season. She and Stewart are old friends, and their easy rapport makes for a lot of laughs. Beals is at her charming, soft-spoken best, gently poking a little fun at Stewart for his slightly breathless inquiries about “research” into lesbian kissing. For those interested in her first Daily Show appearance, go here.

Charlize Theron (Jan. 8, 2004)

When Charlize Theron visited The Daily Show to talk about playing serial killer Aileen Wuornos in Monster, neither she nor Stewart identified Wuornos as a lesbian – unlike most of the media at the time. Wuornos never identified herself as a lesbian, either, but it’s not clear from Theron’s interview with Stewart if that is the reason for their reticence on the subject. Regardless, Theron was obviously sympathetic to the woman she played, and Stewart was clearly in awe of Theron’s performance. If that’s not enough for you, Stewart has interviewed quite a number of the ladies you voted into the AfterEllen.com Hot 100, some of them multiple times. So if you’ve got a spare few hours, here are some links to make you laugh:

Keira Knightley (Hot 100 No. 15) – Nov. 9, 2005

Halle Berry (Hot 100 No. 19) – April 11, 2007

Drew Barrymore (Hot 100 No. 42) – Feb. 12, 2004 and Sept. 13, 2004

Rachel Weisz (Hot 100 No. 44) – April 22, 2003, Feb. 22, 2005 and Aug. 23, 2005

Maggie Gyllenhaal (Hot 100 No. 45) Dec. 15, 2003, July 28, 2005 and Sept. 11, 2006

Meryl Streep (Hot 100 No. 47) – Oct 16, 2007

Maura Tierney (Hot 100 No. 57) – May 14, 2001

Sandra Bullock (Hot 100 No. 64) – March 24, 1999 and Dec 11, 2002

Susan Sarandon (Hot 100 No. 95) – April 8, 2003

Allison Janney (Hot 100 No. 97) – May 16, 2002

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