Drew Barrymore

Lindsey Meeks

Jimmy Fallon

Ben Wrightman

Jason Spevack

Ben - 1980

Jack Kehler

Al

Daniel Greene

Waiter

Ione Skye

Molly

Marissa Jaret Winokur

Sarah

KaDee Strickland

Robin

JoBeth Williams

Maureen Meeks

Siobhan Fallon Hogan

Lana

Evan Helmuth

Troy

Johnny Sneed

Chris

Greta Onieogou

Tammy

Brandon Craggs

Casey

Lenny Clarke

Uncle Carl

Scott Severance

Artie

Jessamy Finet

Theresa

James B. Sikking

Doug Meeks

Willie Garson

Kevin

Armando Riesco

Gerard

Zen Gesner

Steve

Mark Andrada

Ezra

Matt Watts

Valet

Charlotte Sullivan

Spin Instructor

John Franchi

Red Sox Fan

Don Gavin

Cop

Stephen King

Stephen King (uncredited)

Nicholas Purcell

Red Sox Fan (uncredited)

Andrew Wilson

Grant Wade

Martin Roach

Husband