by 
Chelsea Handler is crying. Tucked in the back corner of the restaurant at New York’s Mark Hotel, Handler is dabbing away her tears when a waitress with perhaps the most awkward timing in serving history approaches. She stands dumbstruck at the scene she just walked up to.
“He’s breaking up with me. Can you believe it?” Handler deadpans, still verklempt, gesturing with her snotty napkin across the table at the reporter she’s having brunch with. When the waitress finally walks away, she lets out a big sigh and giggles. “This is like an Oprah Winfrey moment.”
In the grand tradition of Ms. Winfrey, a long conversation about the next phase in the comedian, author, and TV host’s career has meandered through her life’s biggest milestones, striking a surprising emotional chord in the celebrity best known for doling out acid-tongued critiques of Hollywood’s most vapid tabloid mainstays.
Whether it’s in her five New York Times best-selling books, her sold-out stand-up comedy tours, or her seven years hosting the hit E! channel late-night talk show, Chelsea Lately, it’s abundantly clear to both fans and detractors of the 40-year-old performer that Chelsea Handler does not suffer fools. And fools: beware.
As she climbed the ranks, becoming not just the only female talk-show host in late night but among the highest paid people in comedy, Handler honed a brand around her very pointed, very funny comedic middle finger.
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