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Riggle was a member of the United States Marine Corps Reserve and often referred to his military experiences on The Daily Show, including acting as the show's "Military Analyst" and publicly joking that he could kill any other member of the show.
One piece that TV Guide regarded as his signature segment "Marines in Berkeley", a segment in which he dressed in hippie regalia to spoof University of California, Berkeley peace activists protesting a local Marines recruiting station.
He has a long-standing comedic partnership with comedian Rob Huebel with whom he frequently works with at the Upright Citizens Brigade Theater (UCBT) and in their former improvisational sketch comedy troupe Respecto Montalban.
Perhaps the duo's best known creation was their long running two-man show Kung Fu Grip which they often performed at UCBT and other comedy venues for many years.
Riggle and Huebel can also be seen performing a sketch together on stage at the UCBT in Doug Benson's documentary Super High Me.
A featured player during the 2004–2005 season, his first appearance as a cast member was on the show's thirtieth-season premiere on October 2, 2004.
Riggle left The Daily Show on December 10, 2008, in his words "to go fight crime"; however, he appeared at Bonnaroo 2009—along with John Oliver and Rory Albanese, one of the show's executive producers—in a show entitled An Evening (or Afternoon) with The Daily Show featuring John Oliver, Rob Riggle & Rory Albanese.