Plot
Lindsay is stuck in the middle of her relationship with Ben and his passion for the Boston Red Sox.
Trailer
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
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
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
John Boylan
Myerson
J.C. Kenny
Reporter
Paul McGuire
Reporter
Quancetia Hamilton
Rita
Ken Rogerson
Scalper
Howard Nickerson
Usher
George Ghali
Vern - Gym Teacher
Andrea Davis
Wife
Darren Frost
Zach
Sharlene Yuen
Receptionist
Jim Rice
Jim Rice
Dennis Eckersley
Dennis Eckersley
Keith MacWhorter
Keith MacWhorter
Melinda Lopez
Sheri
Sam Dissanayake
Mr. Abdo
Peter Gammons
Peter Gammons
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)
Geoffrey Williamson
High School Kid #1
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
Daniel Cummings
1980's Vendor #2
Jordan Leandre
Jordan Leandre
Bob Weekes
Hot Dog Vendor #1
John Ruggiero
Hot Dog Vendor #2
Joe Buck
Sportscaster
Joe Castiglione
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
Keegan O'Donnell
1980's Batboy
Emily O’Donnell
1980's Fan
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
Stacey Lucchino
Landsdowne Street Fan
Alison Novelli
Landsdowne Street Fan
David Rosenberg
Party Animal
Jesse Peter
East Boston School Kid
Abe Farrelly
East Boston School Kid
Lucy Bidwell
East Boston School Kid
Docky
Crazed Sox Fan
Mariann Neary
Crazed Sox Fan
Paul Palandjian
Fenway Security
Jeanne Zelasko
Jeanne Zelasko
