Rise to Fame
Riggle spent a year on SNL before Jon Stewart's writers figured out what to do with an actual Marine lieutenant colonel who did stand-up: make him the show's embedded military correspondent. His 2006-2008 Daily Show run was the credential that got him into mainstream comedies. The Hangover put him in a cop uniform and had him taser schoolchildren. Step Brothers made him the menacing jock co-worker. The comedic type was set, and Hollywood kept booking him accordingly.
In the Spotlight
The 2020 divorce was the most press Riggle got in years, and not for anything on screen. His estranged wife allegedly planted a hidden camera in his home disguised as a smoke detector, and a court granted him a restraining order after 10,000-plus videos turned up on the device. Holey Moley gave him a TV home through 2022. Since then, he's a utility player: recognizable enough to open a film, not quite a draw on his own.
Side Notes
He was still a Marine reservist while filming the Hangover sequels, retiring as a lieutenant colonel in 2013 after 23 years total. He deployed to Afghanistan twice and worked recovery operations at Ground Zero after 9/11. The odd career crossover: he served under Special Forces commander Max Bowers in Afghanistan, then played Bowers in the 2018 film 12 Strong. He runs an annual golf tournament for wounded veterans, which is about as on-brand as you can get.