Rise to Fame
A tennis injury at 15 rerouted him from sports to a high school stage in Michigan, and from there to NYU, a production assistant gig on Analyze This, commercials, and a short film at SXSW. The real break came with National Treasure in 2004, where he played Riley Poole, the wisecracking tech sidekick opposite Nicolas Cage. The film was a massive hit with a sequel to follow, but the role that embedded him in pop culture was The Hangover in 2009. His character is the engine of the entire plot and barely shows up in the movie.
In the Spotlight
Post-franchise, he settled into the pocket where character actors live: good parts in prestige projects that most people almost watch. His series regular role on The Good Fight kept him on cable for two seasons, while a turn on Godfather of Harlem as Robert Morgenthau showed he could hold real historical weight. The lead turn in Atlanta's 'The Big Payback,' one of Season 3's most discussed episodes, is probably his sharpest recent work. He's now booked on Apple TV+'s Siegfried & Roy limited series, which suggests someone still sees him as more than a supporting act.
Side Notes
Before acting was the plan, he spent over a decade in New York writing commercials and producing an MTV pilot. The acting career happened almost sideways. What makes his Hangover casting genuinely strange is the structure: Doug is the reason the whole movie exists and barely shows up in any of it. He played one of network TV's earlier prominent gay leads in The New Normal (2012), well before that kind of casting became routine. Previously dated Ashley Olsen for about three years, and has kept his personal life mostly quiet ever since.