All Cast

Drew Barrymore
Lindsey Meeks

Jimmy Fallon
Ben Wrightman

Jason Spevack
Ben - 1980

Jack Kehler
Al
Maureen Keiller
Viv

Daniel Greene
Waiter

Ione Skye
Molly

Marissa Jaret Winokur
Sarah

KaDee Strickland
Robin

JoBeth Williams
Maureen Meeks

Siobhan Fallon Hogan
Lana
Brett Murphy
Ryan

Evan Helmuth
Troy

Johnny Sneed
Chris

Greta Onieogou
Tammy
Lizz Alexander
Charlene

Brandon Craggs
Casey
Shary Guthrie
Christie

Lenny Clarke
Uncle Carl
Steve Levy
Reporter at Spring Training

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
Tim McCarver
Tim McCarver

John Franchi
Red Sox Fan

Don Gavin
Cop

Stephen King
Stephen King (uncredited)

Nicholas Purcell
Red Sox Fan (uncredited)

Andrew Wilson
Grant Wade
