This sitcom scene-stealer got her start as a member of the Second City National Touring Company and Chicago's Annoyance Theatre, where she appeared in a slew of popular underground stage shows, including The Real Live Brady Bunch. In the late 1990s, Flannery began popping up on sitcoms, and in 2005, she landed her breakout role as Meredith Palmer, the alcoholic, promiscuous single mom on The Office. Initially cautious about the series' success, Flannery kept her waitressing job throughout the show's first season. Not wanting to abandon her roots in live theater, she performs in the Lampshades, a spoof lounge act that she co-created. Flannery sings in the act, but admits that she shares her singing talent during in-character performances only. Aside from sitcoms and theater, Flannery branches out in many ways: She's been a guest on Iron Chef America, performed on an Air America radio show, was a talent scout for Last Comic Standing and is the musical director of the Los Angeles Drama club, which teaches Shakespeare to young children.