He went on to star in numerous high-profile films, including Almost Famous (2000), Big Fish (2003), Mission: Impossible III (2006), Watchmen (2009), Public Enemies (2009), The Stanford Prison Experiment (2015), Jackie (2016), and Alien: Covenant (2017), in both lead and supporting roles.

Crudup is a four-time Tony Award nominee, winning once for his performance in Tom Stoppard's play The Coast of Utopia in 2007.

[4][5][6] Crudup has spoken of his late father, who died in 2005, as an "incessant gambler and hustler salesman" who continuously sought "to hit the jackpot" throughout his life.

Crudup began acting in films such as 1996's Sleepers, 1997's Inventing the Abbotts, and 1998's Without Limits, where he played the role of running legend and Olympian Steve Prefontaine.

He then played lead guitarist Russell Hammond from Stillwater, the fictional band at the center of Cameron Crowe's Almost Famous (2000).

A year after graduating from Tisch, Crudup made his debut on Broadway in the Lincoln Center Theater production of Tom Stoppard's Arcadia.

[13] In 2011, Crudup received a Tony Award nomination for Featured Actor in a Play for his role in the Broadway revival of Arcadia.

[14] In August 2013, he co-starred with Ian McKellen and Patrick Stewart in the Harold Pinter play No Man's Land as well as in Waiting for Godot at the Berkeley Repertory Theatre.

She was seven months pregnant with their son, William Atticus Parker, born in January 2004, when Crudup ended their relationship and began dating actress Claire Danes.

[19][20] In 2017, Crudup began dating British actress Naomi Watts, after the two met on the set of the Netflix drama series Gypsy.