Robert De Niro as Patrick 'Paddy' Connors

Morgan Freeman as Archibald 'Archie' Clayton

Michael Douglas as Billy Gerson

Kevin Kline as Sam Harris

Mary Steenburgen as Diana Boyle

Jerry Ferrara as Dean

Romany Malco as Lonnie

Roger Bart as Maurice

Joanna Gleason as Miriam Harris

Michael Ealy as Ezra Clayton

Bre Blair as Lisa

April Billingsley as Maid of Honor

Stephen Scott Scarpulla as Danny the Greaser

Andrea Moore as Bachelorette

Dan Hewitt Owens as Security Guard

Edward Edwards as Floor Manager

50 Cent as 50 Cent

Lisa Young as Blackjack Dealer

Ashley Rae Spillers as Elizabeth

Stefan Gordy as Stefan Gordy

Ryan Hartwig as Young Paddy (voice)

Merry Whitney as Party Patron

Violet Chachki as Drag Queen in Pink (uncredited)

Noah Harden as Young Billy

Aaron Bantum as Young Archie

Phillip Wampler as Young Sam

Olivia Stuck as Young Sophie

Andrew Furr as Shufflebot