Drew Barrymore as Lindsey Meeks

Jimmy Fallon as Ben Wrightman

Jason Spevack as Ben - 1980

Jack Kehler as Al

Maureen Keiller as Viv

Daniel Greene as Waiter

Ione Skye as Molly

Marissa Jaret Winokur as Sarah

KaDee Strickland as Robin

JoBeth Williams as Maureen Meeks

Siobhan Fallon Hogan as Lana

Brett Murphy as Ryan

Evan Helmuth as Troy

Johnny Sneed as Chris

Greta Onieogou as Tammy

Lizz Alexander as Charlene

Brandon Craggs as Casey

Shary Guthrie as Christie

Lenny Clarke as Uncle Carl

Steve Levy as Reporter at Spring Training

Scott Severance as Artie

Jessamy Finet as Theresa

James B. Sikking as Doug Meeks

Willie Garson as Kevin

Armando Riesco as Gerard

Zen Gesner as Steve

Mark Andrada as Ezra

Matt Watts as Valet

Charlotte Sullivan as Spin Instructor

Tim McCarver as Tim McCarver

John Franchi as Red Sox Fan

Don Gavin as Cop

Stephen King as Stephen King (uncredited)

Nicholas Purcell as Red Sox Fan (uncredited)

Andrew Wilson as Grant Wade

Martin Roach as Husband

Isabella Fink as Audrey

Miranda Black as Claire

Michael Rubenfeld as Ian

Scott Desano as Binocular Guy

Gina Clayton as Lady at Other Table

Jackie Burroughs as Mrs. Warren

Wayne Flemming as Leon

Bobby Curcuro as Loiterer

Bart Bedford as Man at Other Table

Jason Varitek as Jason Varitek

Johnny Damon as Johnny Damon

Trot Nixon as Trot Nixon

George King as Mr. Munsell

John Boylan as Myerson

J.C. Kenny as Reporter

Paul McGuire as Reporter

Quancetia Hamilton as Rita

Ken Rogerson as Scalper

Howard Nickerson as Usher

George Ghali as Vern - Gym Teacher

Andrea Davis as Wife

Darren Frost as Zach

Sharlene Yuen as Receptionist

Jim Rice as Jim Rice

Dennis Eckersley as Dennis Eckersley

Keith MacWhorter as Keith MacWhorter

Melinda Lopez as Sheri

Sam Dissanayake as Mr. Abdo

Peter Gammons as Peter Gammons

Don Orsillo as Don Orsillo

Harold Reynolds as Harold Reynolds

Bob Lobel as Bob Lobel

Carl Beane as Stadium Announcer (voice)

Mathew Peart as High School Kid #2 (as Matthew Peart)

Geoffrey Williamson as High School Kid #1

David Klar as High School Kid #3

Jermaine Plummer as High School Kid #4

Erin Nanstad as Female Fan

Johnny Cicco as Bleacher Fan

Brian Hayes Currie as Screaming Fan

Danny Murphy as 1980's Vendor #1

Daniel Cummings as 1980's Vendor #2

Jordan Leandre as Jordan Leandre

Bob Weekes as Hot Dog Vendor #1

John Ruggiero as Hot Dog Vendor #2

Joe Buck as Sportscaster

Joe Castiglione as Sportscaster

Thomas Jordan as Kid in Cast (as Tommy Jordan)

Preston Thomas as 1980's Sox Player

Scott Rosenberg as 1980's Sox Player

Mark Ciardi as 1980's Sox Player

Keegan O'Donnell as 1980's Batboy

Emily O’Donnell as 1980's Fan

Diana O'Donnell as 1980's Fan

Meda Thomas as 1980's Fan

Jack Andrade as 1980's Fan

Warren Tashjian as 1980's Fan

Ray 'Rocket' Valliere as 1980's Fan

Bob Sands as Landsdowne Street Fan

Stacey Lucchino as Landsdowne Street Fan

Alison Novelli as Landsdowne Street Fan

David Rosenberg as Party Animal

Jesse Peter as East Boston School Kid

Abe Farrelly as East Boston School Kid

Lucy Bidwell as East Boston School Kid

Docky as Crazed Sox Fan

Mariann Neary as Crazed Sox Fan

Paul Palandjian as Fenway Security

Jeanne Zelasko as Jeanne Zelasko