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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.
While Ferrell and Stewart began discussing Riggle's "lack of talent" and making other disparaging remarks about him, Riggle suddenly walked onto the set to surprise them and asks if they were talking about him.
Riggle's intimidating presence appears to make Ferrell and Stewart visibly afraid, continuing the running-joke that Stewart is very afraid of Riggle.
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.
Prior to being hired as a cast member, Riggle also appeared in a non-speaking role in the previous season (season 29) in a pre-taped parody of Fear Factor.
The duo's growing popularity landed them an audition on Saturday Night Live in the summer of 2004.
They auditioned together, though only Riggle ended up making the cut.
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.
On August 3, 2010, Riggle made a surprise cameo on The Daily Show during an interview with Will Ferrell.