Mark Webber as William Harding

Catalina Sandino Moreno as Sarah

Sônia Braga as Mrs. Garcia

Ethan Hawke as Vince

Josh Zuckerman as Decker

Laura Linney as Jesse

Michelle Williams as Samantha

Daniel Ross Owens as Young Vince (as Daniel Ross)

Glen Powell as John Jagerman (as Glen Powell, Jr.)

Anne Clarke as Young Jesse

Cherami Leigh as Danielle

Jesse Harris as Dave Afton

Bill Dobrow as Drummer

Jon Fowler as Bassist

Guyora Kats as Pianist/Accordian Player

Nick McDonnel as Artsy Guy

Alexandra Daddario as Kim

Jonathan Marc Sherman as Party Philosopher

Richard Linklater as John Wayne Enthusiast

Ryan Hawke as Williamsburg Hip Girl (as Ryan Shawhughes)

Iraida Polanco as Proprietor

Gabriel Rivera as Guitar Player

Greta Gaines as Faye

Frank Whaley as Harris

Lynn Cohen as Harris's Mother

John Patrick Shanley as Priest

Elissabeth Blofson as Kissing Couple

Ben Dickey as Kissing Couple (as Benjamin Dickey)

Lara Theodos as Waitress