Amy Schumer's tour comes to Chicago

The raunchy and hilarious stand-up comedian is on a roll.

Photograph: Natalie Brasington

Amy Schumer can’t lose. When we speak via telephone on a recent Friday, she is hours away from kicking off Inside Amy Schumer: The Live Tour, a night of stand-up comedy at the Mirage in Las Vegas that coincides with the debut of her upcoming Comedy Central show, Inside Amy Schumer. After killing it on the road for many years and grabbing headlines at the roasts of Charlie Sheen and Roseanne Barr, Schumer is on a winning streak (to use Vegas speak) that will continue Friday 8 when she plays to a sold-out house at the Vic Theatre. But she also literally cannot afford a loss while in Sin City. “I love playing craps and poker and blackjack,” Schumer says. “It’s a little weirder now because I’ll get recognized and it makes it more embarrassing when you lose.”

Schumer was born in Manhattan and raised on Long Island. Her dad’s cousin is U.S. Senator Chuck Schumer (D-NY). Although she claims no intimate connection to the senator, en route to Vegas she just missed him at the airport’s Delta Lounge. “I was like, ‘Ah, man, that would’ve been a fun Instagram thing.’ ” In 2004, she began practicing stand-up in New York and has been slowly gaining steam, first as a contestant on the fifth season of NBC’s Last Comic Standing in 2007 where she placed fourth and more recently, well, just about everywhere.

There’s a reason for this. At 31, Schumer is finally perfectly suited for her self-deprecating style of humor focused on sexual mores. Onstage, she plays the prototypical thirtysomething woman, still unmarried (although she’s currently dating stand-up comedian Anthony Jeselnik) and wondering aloud if she’s the whore in her group of friends or if it’s okay to take it up the butt. “I would like to move away from sex,” Schumer says. “I swear to you, it’s not a gimmick. It’s not a choice; it’s just what’s always interested me.” For the perfect Schumer sampling, download her 2011 album Cutting on iTunes or check out her 2012 Comedy Central special Mostly Sex Stuff, where in between her musings on birth control and overbearing mothers, Schumer drops catchy one liners like, “ I’ve only slept with four people…that was a weird night,” or “I finally slept with my high school crush…but now he expects me to go to his graduation…like I know where I’ll be in three years.”

Schumer’s candid talk has a point—even though it’s cloaked in outrageous absurdity. She’s among a growing cadre of female comedians speaking openly about sex. “It’s good to hear a woman publicly saying, ‘Yeah, I have slept with people that weren’t my boyfriend and I do have HPV,’ ” says Schumer. “I haven’t been living this perfect life and I’ve made sexual mistakes and I’ve been racist by accident. I wish I’d seen a girl talking about this stuff when I was younger.”

Fans locked out of her sold-out Friday show can still get their fix with Inside Amy Schumer debuting in April on Comedy Central. The show is a mix of interviews, stand-up, man-on-the-street segments and sketches where Schumer plays a fictional version of herself getting into trouble (like when she has to walk away from a gang bang). If Schumer’s winning streak continues, her show is going to kill, and I have a feeling it will. Again, to use Vegas speak, she’s what I’d call a sure bet.

Inside Amy Schumer: The Live Tour happens Friday 8.

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