Max Casella

Ryan

Kate Winslet

Ginny

Jim Belushi

Humpty

David Krumholtz

Jake

Justin Timberlake

Mickey Rubin

Woody Allen

Director

Jack Gore

Richie

Steve Schirripa

Nick

Debi Mazar

Birthday Party Guest

Tony Sirico

Angelo

Tom Guiry

Flirtatious Man at Ruby's

Juno Temple

Carolina

Maddie Corman

Psychiatrist

Bobby Slayton

Fishing Buddy

Jenna Stern

Tiny

Ed Jewett

Ruby's Customer

Tommy Nohilly

Humpty's Friend

Robert C. Kirk

Boardwalk Vendor

Ron Chez

Executive Producer

John Doumanian

Ruby's Bartender

Gregory Dann

Fishing Buddy

Michael Zegarski

Fishing Buddy

Geneva Carr

Mary

Danielle Ferland

Birthday Party Guest

Jacob Berger

Watch Salesman

Michael Striano

Sailor on Phone

Adam B. Stern

Executive Producer

Mark Attanasio

Executive Producer