Chelsea Handler Talks Hating Fashion & Her Waitressing Days With Paper Magazine

Jason Scott
March 10, 2014

There is absolutely no one quite like Chelsea Handler. She's witty, sharp, overdramatic and not afraid to speak her mind, no matter how offensive it may be. But it's all with good intentions, though, despite the mounds of wealth now laying at her feet. Of course, she wasn't always on top. Back in the day, she began a string of nine waitressing jobs, from the time she was 19 to 27. "I was the biggest bitch," she reveals to Paper Magazine in their spring issue.

"I didn't understand people who wouldn't look you in the eye and tipped before tax," she adds, sheepishly. "Do you have any idea the kind of tips I leave? How you make someone feel when they get a $100 tip on a drink?"

Even if she herself received whopping tips, she didn't exactly know how to save money. She explains, "I would go to San Francisco and lose money on my week because you have to put yourself up at a decent hotel if you don't want to be, like, staying with drug dealers and prostitutes."

Of course, she now runs her own E! talk show, Chelsea Lately, and has published multiple books, including Are You There, Vodka? It's Me Chelsea. In 2010, Forbes named her one of the Celebrity 100, reporting her income as $19 million. Needless to say, money is no longer a problem. “Life has become so ridiculous because I have access to such nonsense and I can go to these places. I’ve become so infantilized by having so many assistants — people who take care of you and pack for you and dress you. It just never stops. It’s very random nonsense but I’m glad to have it.”

"We stay in places based on how they make a margarita," she quips. "I call ahead and have my assistant talk to them. I'm seriously on the border of turning into Jennifer Lopez. That's what I think of myself."

But through it all, Handler stays true to herself, never once coming off fake or ever wanting to be. Many Hollywood-ites might relish in red carpets and looking good for the camera, but she admits that she finds fashion and fashion reviews "utterly ridiculous." She details: "I'm interested in looking good for me, but I'm not interested in going to a fashion show. It's not real. I went once last year with a boyfriend. I was like, 'This is the worst nightmare I could have ever been to.' I was embarrassed to be there."

Case in point: 2012's Vogue Met Ball proved to be a nightmare experience for the comedian. "I was like, 'Why am I here?'" she reminisces. "I didn't have fun."

She continues, "I have no idea what the theme was, nor did I care. I know that I wore motorcycle boots under my Roland Mouret gown. I think it was a Roland Mouret and Anna Wintour was like, 'She cannot wear motorcycle boots.' I'm like, 'Well then I'll wear them so I can guarantee never getting invited again.'"

Check out the entire interview over on Paper Magazine!

Join Our Fantasy Trading Community
Become a Wall Street Trader
Leave this field empty

By clicking Sign Up, you agree to our terms and conditions and have read and understand our privacy policy.