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

Martin Roach

Husband

Isabella Fink

Audrey

Miranda Black

Claire

Michael Rubenfeld

Ian

Scott Desano

Binocular Guy

Gina Clayton

Lady at Other Table

Jackie Burroughs

Mrs. Warren

Bart Bedford

Man at Other Table

Johnny Damon

Johnny Damon

George King

Mr. Munsell

John Boylan

Myerson

J.C. Kenny

Reporter

Quancetia Hamilton

Rita

Ken Rogerson

Scalper

Andrea Davis

Wife

Darren Frost

Zach

Peter Gammons

Peter Gammons

Johnny Cicco

Bleacher Fan

Brian Hayes Currie

Screaming Fan

Danny Murphy

1980's Vendor #1

Joe Buck

Sportscaster

Thomas Jordan

Kid in Cast (as Tommy Jordan)

Preston Thomas

1980's Sox Player

Scott Rosenberg

1980's Sox Player

Mark Ciardi

1980's Sox Player

Warren Tashjian

1980's Fan

Ray 'Rocket' Valliere

1980's Fan

Abe Farrelly

East Boston School Kid

Mariann Neary

Crazed Sox Fan