Growing up in the humble Midwestern town of Rockford, Ill., one-time Harlem resident actress and comedian Natasha Leggero wasn’t ushered into the higher reaches of the entertainment industry through nepotism or fortuitous personal connections.
From a private lounge inside San Francisco’s Bill Graham Civic Auditorium where she and a pantheon of elite comedians performed at Comedy Central’s inaugural Colossal Clusterfest earlier this month, Leggero recalls a childhood that bore a likeness to the hit ABC television series Roseanne.
“I would say [we were] lower-middle-class, but I feel like my mom would start crying if she heard that,” Leggero says. “But my dad was a used car dealer and my mother worked in a locksmith shop as the bookkeeper, and then they got divorced, and I do remember, like, nuns bringing us food–like big canned goods. And then, you know, we didn’t really go on vacation–ever. We went to Florida once, to [Disney World], with my mom’s boyfriend at the time. But then apart from that, no vacations, we just kinda stayed in Illinois. I didn’t know England was an island, I think until I was like 23 and went there. I was pretty poor. I had so many jobs growing up: I mowed lawns; I worked at a grocery store; I had two newspaper routes; I worked at a catering place… I definitely hustled.”
Projecting an air of mock-refinement and elitism as a standup, the 43-year-old comedian and star of Comedy Central’s Another Period often accentuates her striking beauty with an elegant wardrobe befitting a duplicitous trophy wife. Accordingly, one wonders if this persona was intentionally crafted to spawn a “bizarro” version of her bygone selves. Like her childhood–where she has hazy recollections of sharing McDonald’s cheeseburgers with her siblings–Leggero’s young adult years were also colored by a distinct lack of money and the crafty ways one must compensate to survive.
“I got a theater scholarship to Illinois State University, but I was very poor in college,” Leggero says. “I got a meal plan that was only Monday through Friday because I had to pay for everything on my own, and then Saturday-Sunday I would stay in town and get a loaf of bread at the Italian bakery and just eat on that all weekend. I [also] worked in the cafeteria, so I got some free food there–took some stuff home. It was pretty nasty. And then I moved to New York, and I remember my relationship with money then was definitely however much you had in your account, that’s what you’d spend that day. But I always had a very open and free relationship with my money: I remember once it was my friend’s birthday and I had $12 in my account and I was like, ‘F**k it! I’ll buy you a drink!’ I would always spend everything I had.”
This year at Clusterfest, Leggero’s name was emblazoned on promo materials large and small alongside comedy kingpins Jerry Seinfeld, Kevin Hart, Sarah Silverman and many more. And like any good success story that arises from total obscurity, her ascension to the big stage proved a combination of talent, dedication and likely a few strokes of luck.
One momentous example of good fortune along her path to stardom? You guessed it: predatory lending.
…I lived in Harlem. I was waitressing. I couldn’t get an agent. Every day I would wake up and pound the pavement to no avail.
“New York was proving itself to be so hard for me. I lived in Harlem. I was waitressing. I couldn’t get an agent. Every day I would wake up and pound the pavement to no avail. And then I got this letter from Chase Manhattan bank–my bank where I was storing my $12–and they were like, ‘Here’s $5,000 overdraft protection on your account (laughs)!’ I mean, this was a long time ago, and then I was like, ‘Oh! I’ll move to LA!’ So I took that $5,000 with my checkbook and just wrote checks to get myself to LA… Definitely, I don’t regret it because it totally helped me–and then I slowly started to get some things happening. Do you wanna know how much money I have in my account now?”(Sadly, the offer was in jest.)
Now with years of recognition and success at her back, she and husband Moshe Kasher (a fellow comedian and host of Comedy Central’s late-night talk show, Problematic with Moshe Kasher) live comfortably on their combined funny money–although her spending habits can be too undisciplined for his taste. And in addition to sinking cash into nice vacations and posh hotels, Leggero cites a snippet from her act about the ease and twisted beauty of Amazon.
“With Amazon, the way I shop now is way different. I used to go shopping and compare prices and see how much things cost and maybe come back the next day. Now I just sit in my house and smoke some pot and dream things up, and then they exist! Gold stapler! All the dogs need eye patches! I get really stupid stuff. I’ve definitely gotten sunscreens from around the world arriving constantly. Yeah, my husband said no more European sunscreens.”
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