He was the first person to be a cast member on both FOX's MADtv and its rival sketch show, NBC's Saturday Night Live, appearing on the former in 2000, and the latter from 2001 to 2004.

[3][4][5] As a standup comedian, Richards has opened for Chris Kattan, Andrew Dice Clay, Rob Schneider, David Spade, Louie Anderson, and Andy Dick.

He has appeared as a guest on Marc Maron's WTF podcast, and Kill Tony, as well as on Aqua Teen Hunger Force and NBC's Late Night.

[9][10] He then attended the University of North Carolina at Chapel Hill (UNC) and, in his senior year, he joined the improvisational comedy team CHiPs Improv.

The following year Richards joined the cast of Saturday Night Live during its 27th season, making him the first person to be a cast-member of both sketch comedy shows (Taran Killam would later become the only other performer to do so).

[3][11] In 2004 Richards appeared in the Comedy Central year-end retrospective special Last Laugh '04 as Fox News commentator Bill O'Reilly.

As reported in Entertainment Weekly,[15] Richards recently launched his own podcast, featuring one of his impressions interviewing celebrity guests.