Rise to Fame
In 2002, he appeared in three Best Picture nominees: Chicago, Gangs of New York, and The Hours. That kind of density doesn't happen by accident. He'd spent the 1990s building as a serious ensemble player through Paul Thomas Anderson's first three films, and Peter Travers called him 'the heart of Magnolia,' yet he got no Oscar nomination for that. Chicago gave him his one nod, playing Roxanne's doormat husband Amos Hart. He lost to Chris Cooper, but the nomination confirmed what the industry already knew.
In the Spotlight
The Oscar-Grammy-Tony trifecta puts him in vanishingly rare company, and none of those nominations came from the same career phase. He pivoted from Paul Thomas Anderson dramas to Will Ferrell comedies, somehow without losing either audience. Walk Hard earned him a Grammy nomination for co-writing the title song. Stan & Ollie had him wearing prosthetics as Oliver Hardy and earning a Golden Globe nomination. The Mister Romantic project released its debut album in June 2025. He keeps reinventing the act without abandoning what came before.
Side Notes
Nobody on the street knew they were being interviewed by a movie star. That was the entire premise of Dr. Steve Brule: he'd show up to Tim and Eric tapings with his own costume, his own hair, and improvise everything, no writers' room required. Subjects sat across from him with no idea who he was. Reilly created Brule from scratch and spun him off into four Adult Swim seasons. He still insists, with a straight face, that he and Brule have never actually met.