[1] Her observational comedy has been noted by critics for its use of satire, as commentary on such themes as celebrity culture and social class.

[citation needed] Leggero was born on March 26, 1974[a] in Rockford, Illinois[5] and is of Italian[6] and Swedish[7] descent.

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... we didn't really go on vacation–ever...

Instead Leggero went to an acting class which was taught by the brother of the artistic director of New American Theatre on Main Street in Rockford.

While at Illinois State, Leggero auditioned for the Stella Adler Conservatory in Chicago and was accepted into the theater program.

She then went to New York City to attend the conservatory, studying for two years and living in a rent controlled apartment.

[11] In 1996, she moved to Sydney, Australia with her then-boyfriend who nicknamed her "Weiner" and lived there for eight months before returning to New York[12] to attend Hunter College.

Leggero shot an unaired pilot called The Strip for NBC with Tom Lennon and Ben Garant.

Along with Andy Kindler and Greg Giraldo, she was a judge on the 2010 season of NBC's Last Comic Standing, which was hosted by Craig Robinson.

[16] In August 2015, she debuted her Comedy Central standup special, Live at Bimbo's (originally entitled Diamond P__), which was filmed in San Francisco.

[19] In 2016 and 2017, Leggero and husband Moshe Kasher embarked on The Honeymoon Tour, in which they performed stand-up shows and provided humorous relationship advice throughout the United States.

[24] Her approach to standup has been noted for its heavy use of persona, which largely relies on costumes and "an air of mock-refinement and elitism.

"[2] Journalist John Wenzel wrote that Leggero's use of persona allows her to "indict the most bloated, superficial aspects of our culture.

[26]On January 20, 2024, Leggero surprised an audience at The Improv in Los Angeles, when she flashed the crowd to impersonate comedian Bert Kreischer after his act.

[30] In 2015 Leggero and Moshe Kasher bought a home in the Silver Lake area of Los Angeles.