Drew Barrymore ... Lindsey
Jimmy Fallon ... Ben
Jason Spevack ... Ben - 1980
Jack Kehler ... Al
Scott Severance ... Artie (as Scott H. Severance)
Jessamy Finet ... Teresa (as Jessamy R. Finét)
Maureen Keiller ... Viv
Lenny Clarke ... Uncle Carl
Ione Skye ... Molly
KaDee Strickland ... Robin
Marissa Jaret Winokur ... Sarah
Evan Helmuth ... Troy
Brandon Craggs ... Casey
Brett Murphy ... Ryan
Isabella Fink ... Audrey
Miranda Black ... Carrie
Greta Onieogou ... Tammy
Johnny Sneed ... Chris
James Sikking ... Doug Meeks (as James B. Sikking)
Michael Rubenfeld ... Ian
Willie Garson ... Kevin
Armando Riesco ... Gerard
Zen Gesner ... Steve
Siobhan Fallon Hogan ... Lana
JoBeth Williams ... Maureen Meeks
Mark Andrada ... Ezra
Charlotte Sullivan ... Spin Instructor
Scott Desano ... Binocular Guy (as Scott DeSano)
Lizz Alexander ... Charlene
Shary Guthrie ... Christie
Don Gavin ... Cop
Andrew Wilson ... Grant Wade
Martin Roach ... Husband
Gina Clayton ... Lady at Other Table
Wayne Flemming ... Leon
Bobby Curcuro ... Loiterer
Bart Bedford ... Man at Other Table
Jason Varitek ... Jason Varitek
Johnny Damon ... Johnny Damon
Trot Nixon ... Trot Nixon
George King ... Mr. Munsell
Jackie Burroughs ... Mrs. Warren
John Boylan ... Myerson
J.C. Kenny ... Reporter
Paul McGuire ... Reporter
Quancetia Hamilton ... Rita
Ken Rogerson ... Scalper
Howard Nickerson ... Usher
Matt Watts ... Valet
George Ghali ... Vern - Gym Teacher
Andrea Davis ... Wife
Darren Frost ... Zach
Sharlene Yuen ... Receptionist
Geoffrey Williamson ... High School Kid #1
Jim Rice ... Jim Rice
Dennis Eckersley ... Dennis Eckersley
Keith MacWhorter ... Keith MacWhorter
Melinda Lopez ... Sheri
Sam Dissanayake ... Mr. Abdo
Peter Gammons ... Peter Gammons
Steve Levy ... Reporter at Spring Training
Tim McCarver ... Tim McCarver
Don Orsillo ... Don Orsillo
Harold Reynolds ... Harold Reynolds
Bob Lobel ... Bob Lobel
Carl Beane ... Stadium Announcer (voice)
Mathew Peart ... High School Kid #2 (as Matthew Peart)
David Klar ... High School Kid #3
Jermaine Plummer ... High School Kid #4
Erin Nanstad ... Female Fan
Johnny Cicco ... Bleacher Fan
Brian Hayes Currie ... Screaming Fan
Danny Murphy ... 1980's Vendor #1
Dan Cummings ... 1980's Vendor #2
Daniel Greene ... Waiter
Jordan Leandre ... Jordan Leandre
Bob Weekes ... Hot Dog Vendor #1
John Ruggiero ... Hot Dog Vendor #2
Joe Buck ... Sportscaster
Joe Castiglione ... Sportscaster
Tommy Jordan ... Kid in Cast
Preston Thomas ... 1980's Sox Player
Scott Rosenberg ... 1980's Sox Player
Mark Ciardi ... 1980's Sox Player
Keegan O'Donnell ... 1980's Batboy
Emily O'Donnell ... 1980's Fan (as Emily)
Diana O'Donnell ... 1980's Fan
Meda Thomas ... 1980's Fan
Jack Andrade ... 1980's Fan
Warren Tashjian ... 1980's Fan
Ray 'Rocket' Valliere ... 1980's Fan
Bob Sands ... Landsdowne Street Fan
Corey Sands ... Landsdowne Street Fan
Andrew Steedman ... Landsdowne Street Fan (as Andrew)
Mike Steedman ... Landsdowne Street Fan
Davis Ballard ... Landsdowne Street Fan
Blair Ballard ... Landsdowne Street Fan
Stacey Lucchino ... Landsdowne Street Fan
Marla Angermeier ... Landsdowne Street Fan
Alison Novelli ... Landsdowne Street Fan
Mari Corcoran ... Landsdowne Street Fan
David Rosenberg ... Party Animal
Rick Cohen ... Party Animal
Jesse Peter ... East Boston School Kid
A.B. Farrelly ... East Boston School Kid (as Anna Byers)
Lucy Bidwell ... East Boston School Kid
Joan Macleod-Follows ... Lindsey's Co-Worker
Bobbi Stoller ... Crazed Sox Fan
Brad Blank ... Crazed Sox Fan
Todd Abbrecht ... Crazed Sox Fan
Monica Niedermeyer ... Crazed Sox Fan
Jenna Caswell ... Crazed Sox Fan
Amie James ... Crazed Sox Fan
Matt Melina ... Crazed Sox Fan
Jaime P. Ford ... Crazed Sox Fan
Christine Ford ... Crazed Sox Fan
Docky ... Crazed Sox Fan
Mariann Neary ... Crazed Sox Fan
Sam Caswell ... World's Greatest Sox Fan
Ron 'Puppy' Cavallo ... Bleacher Bum
Paul Palandjian ... Fenway Security