Big Gay Following: Chelsea Handler

Her second book, Are You There, Vodka? It's Me, Chelsea, may have topped the New York Times best-seller list, but when it comes to gay men, Chelsea Handler prefers bottoms. The brassy star of E!'s late-night chat show Chelsea Lately certainly had a bunch at her beck and call this year as Queen of West Hollywood's Halloween Carnaval and as host of November's Out 100 gala in New York City. Here, the 33-year-old New Jersey native encourages stereotypes, Lindsay's sapphic romance, and overturning Proposition 8.

The Advocate: How do you explain your strong connection with the gay community?
Chelsea Handler: I'm like a gay man trapped in a woman's body, and that's exactly why the gays and I get along so well. We have the same attitude, which is "fuck everybody and let's say exactly what we think." I understand somebody who doesn't exactly fit in, somebody who's struggled or felt embarrassed, ashamed, or not confident in who they are. Growing up, I got tortured and made fun of, but that makes you a lot stronger. And now, obviously, I'm very popular.

When did you first feel love from gays?
When I had sex with my first gay man. It was pretty quick and painless, but I definitely felt it. [Laughs] I was never some fruit fly hanging around with a bunch of gay guys. I always just loved gay people. Now I definitely have friends and people on staff who are gay, but I don't only hang around gay people. It's not like I'm trying to be Tori Spelling -- on many levels.

Long before Paris Hilton was searching for a BFF, you interviewed potential gay besties on your previous E! series, The Chelsea Handler Show. What qualities do you look for in a gay pal?
I like bottoms. [Laughs] I don't like catty gay guys who are like, "She did this and that," and act like women. It's like, You're still a man. Act like a man.

Chelsea Lately recently featured an all-gay discussion panel with comics Scott Thompson and Guy Branum, plus singer Justin Tranter. How did it compare to a regular panel?
We did a theme week with a redheaded panel, a black panel, and a fat-ass panel, but "gay day" was definitely the best. Gay people just have a better sense of humor. The kindred spirit thing also lies there.

With which gay celebrity would you most like to grab a drink?
I'm not as much into gay celebrities as I am just into gay people. I like how effusive they are. They're more fun to be around, they laugh harder, they cry louder, and they do everything with a little more oomph. I grew up in a Jewish family, so there wasn't a lot of emotion running around.

But your late mother was Mormon. Did that affect your thoughts on homosexuality?
Well, we kept the Mormon side down to a dull roar growing up, because we realized how ridiculous and intolerant that religion is. My mom was never really a typical devout Mormon. After my brother passed away when he was 21 years old, my mom turned to religion, as many people do, but she was very tolerant of other religions. It was a melding of religions in our household, which worked out well because we're all open to anything -- and, as a final result, not religious at all. Organized religion, more than anything else, is completely inappropriate.

It was definitely un-Mormon of you to donate $5,000 toward defeating Prop. 8.
It's really upsetting and annoying that it passed. It's all because of the religious right, and it's very disappointing. If you don't believe in gay marriage, don't get married to a gay person; there's no reason you should prevent another person from doing it. You don't go back on civil rights. Can you imagine if we said, "OK, slavery is legal again"? No. For something like that to be overturned is ridiculous.

Should Ellen and Portia return their wedding gifts?
Well, hopefully they weren't registered for gifts in the first place, because Ellen's probably one of the highest-paid gay people in the world.

Did you attend any Prop. 8 protests or rallies?
I only go where the gay people invite me to go. It's not nice to do things for the community only when people are looking. People who speak out for gay people just so that they can create a fan base annoy the shit out of me. People like Tori Spelling. She doesn't have compassion for them. She's not going out doing things for them. She's like, "Oh, I have such a huge gay following." It's because no one else is following her!

How do you feel about the word "fag" as a comedian?
I think it's a word you can use in jest with somebody who's gay. When you say anything with hatred and maliciousness, yes, it comes off bad. But if you say it in a jocular manner, you can get away with a lot. If someone called me a "cheap Jew" while smiling and rubbing my shoulders, I'd have a lot less of a problem than if they just came up and called me a "kike." It's all in your delivery and your comfort level with another person. I don't think you can outlaw words, although there are some words you should never use: You can never say the n word. But we have to be able to laugh at each other, so we have to find a way to make fun of other people and ourselves. And stereotypes are funny. It's funny that black people are late.

Do you consider any topic taboo?
I try not to make fun of anybody if they're going to rehab for the first time. If they're going for the second or third time, then all bets are off. And I don't think death is that funny. I mean, after a couple of months it can be hysterical, but not right away.

Speaking of rehab, Lindsay Lohan finally admitted her love for Samantha Ronson yet denied that she's a lesbian. What's her deal?
That girl just needs attention and someone to love her. People who come from screwed-up families look for it anywhere they can get it. Those girls end up being so lonely -- the Britneys, Parises, and Lindsays. Well, Paris isn't as lonely because she just sleeps with everybody, so that fills her up for a little bit -- literally and metaphorically. Lindsay is so confused and so not a full-grown person. It would be great if this whole thing with Samantha works, but I don't think she knows what she is. She's just young and not the sharpest tool in the shed.

Have you ever gone through a lesbian phase?
Not for more than, like, one night. It ended with me leaving in the middle of the night, saying, "Uh, no, it's not my turn."

You and your diminutive assistant Chuy were crowned queen and king of the 2008 West Hollywood Halloween Carnaval. What were your royal duties?
I basically had to show up, get coronated, and say a few words. Then I left Chuy in a sea of gay people while I went off to have a respectable dinner. It was very dangerous because everybody was jumping on our golf cart trying to get a piece of him, so I said, "You should leave with me and come to dinner." He said, "No, no, I want to stay and say hello to my fans." Cut to him not being able to get a car out of there until, like, 4 a.m.

Ever secretly wish that Chuy were gay?
Yeah, every time he puts his hand up my skirt.