Leggero began performing at age 10, in several Chicago plays. After graduating from high school, she moved to New York City to study at the Stella Adler Conservatory. While there, she also attended Hunter College and received her B.A. in theater criticism. She moved to Los Angeles shortly after graduation and started dating fellow comedian Ari Shaffir.
As of 2009, Leggero is a frequent roundtable panelist on friend Chelsea Handler's late-night talk show Chelsea Lately.
Her stand-up television appearances include performances on The Tonight Show with Jay Leno, The Late Late Show with Craig Kilborn, Last Call with Carson Daly, and she has appeared on multiple Comedy Central stand-up programs, including the animated show Ugly Americans, where she voices Callie Maggotbone.
She has performed at such festivals as SXSW, the Sasquatch Music Festival and the prestigious Montreal Comedy Festival.
Leggero shot an unaired pilot called, The Strip, for NBC, with Tom Lennon and Ben Garant from Reno 911! She was a judge, alongside Andy Kindler and Greg Giraldo, on the 2010 season of NBC’s, Last Comic Standing, hosted by Craig Robinson. Leggero played Emma in NBC's 2011 sitcom Free Agents. From 2010 to January 2012, Leggero co-hosted The Lavender Hour podcast with her boyfriend at the time - comedian Duncan Trussell. On February 17, 2012, she appeared on the Adam Carolla Show.
In 2012, Leggero began being featured in episodes of NBC's Are You There, Chelsea? as Nikki, Rick the bar manager's ex-girlfriend. Leggero was featured in every first-season episode starting with the second episode, "Sloane's Ex." Also in 2012 she played the sex freak Haley in the web series Burning Love, a spoof of the TV series The Bachelor and The Bachelorette.
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