Billy Crudup, Natasha Lyonne, and Robert Khakh in Everyone Says I Love You (1996)

Billy Crudup and Natasha Lyonne in Everyone Says I Love You (1996)

Jennifer Aniston, Reese Witherspoon, and Billy Crudup in It's Like the Flu (2021)

Jennifer Aniston, Reese Witherspoon, and Billy Crudup in The Morning Show (2019)

Billy Crudup and Greta Lee in The Morning Show (2019)

Billy Crudup in 20th Century Women (2016)

Billy Crudup and Greta Gerwig in 20th Century Women (2016)

Billy Crudup, Tom Irwin, and Hayes MacArthur in The Morning Show (2019)

Billy Crudup and Emma Nelson in Where'd You Go, Bernadette (2019)

Billy Crudup and Mandy Moore in Dedication (2007)

Billy Crudup and Jack Black in Jesus' Son (1999)

Cate Blanchett and Billy Crudup in Charlotte Gray (2001)

Billy Crudup and Mark Duplass in Fever (2021)

Billy Crudup and Monica Potter in Without Limits (1998)

Claire Danes and Billy Crudup in Stage Beauty (2004)

David Duchovny, Julianne Moore, Billy Crudup, and Maggie Gyllenhaal in Trust the Man (2005)