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Cast (105)
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
B.M
Brett Murphy
as Ryan
Evan Helmuth
as Troy
Johnny Sneed
as Chris
Greta Onieogou
as Tammy
L.A
Lizz Alexander
as Charlene
Brandon Craggs
as Casey
S.G
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
T.M
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
M.B
Miranda Black
as Claire
M.R
Michael Rubenfeld
as Ian
S.D
Scott Desano
as Binocular Guy
G.C
Gina Clayton
as Lady at Other Table
Jackie Burroughs
as Mrs. Warren
W.F
Wayne Flemming
as Leon
B.C
Bobby Curcuro
as Loiterer
B.B
Bart Bedford
as Man at Other Table
J.V
Jason Varitek
as Jason Varitek
J.D
Johnny Damon
as Johnny Damon
T.N
Trot Nixon
as Trot Nixon
G.K
George King
as Mr. Munsell
John Boylan
as Myerson
J.K
J.C. Kenny
as Reporter
P.M
Paul McGuire
as Reporter
Q.H
Quancetia Hamilton
as Rita
K.R
Ken Rogerson
as Scalper
H.N
Howard Nickerson
as Usher
G.G
George Ghali
as Vern - Gym Teacher
Andrea Davis
as Wife
D.F
Darren Frost
as Zach
S.Y
Sharlene Yuen
as Receptionist
J.R
Jim Rice
as Jim Rice
D.E
Dennis Eckersley
as Dennis Eckersley
K.M
Keith MacWhorter
as Keith MacWhorter
M.L
Melinda Lopez
as Sheri
Sam Dissanayake
as Mr. Abdo
P.G
Peter Gammons
as Peter Gammons
D.O
Don Orsillo
as Don Orsillo
H.R
Harold Reynolds
as Harold Reynolds
B.L
Bob Lobel
as Bob Lobel
C.B
Carl Beane
as Stadium Announcer (voice)
M.P
Mathew Peart
as High School Kid #2 (as Matthew Peart)
G.W
Geoffrey Williamson
as High School Kid #1
D.K
David Klar
as High School Kid #3
J.P
Jermaine Plummer
as High School Kid #4
E.N
Erin Nanstad
as Female Fan
Johnny Cicco
as Bleacher Fan
Brian Hayes Currie
as Screaming Fan
Danny Murphy
as 1980's Vendor #1
D.C
Daniel Cummings
as 1980's Vendor #2
J.L
Jordan Leandre
as Jordan Leandre
B.W
Bob Weekes
as Hot Dog Vendor #1
J.R
John Ruggiero
as Hot Dog Vendor #2
Joe Buck
as Sportscaster
J.C
Joe Castiglione
as Sportscaster
T.J
Thomas Jordan
as Kid in Cast (as Tommy Jordan)
Preston Thomas
as 1980's Sox Player
Scott Rosenberg
as 1980's Sox Player
M.C
Mark Ciardi
as 1980's Sox Player
K.O
Keegan O'Donnell
as 1980's Batboy
E.O
Emily O’Donnell
as 1980's Fan
D.O
Diana O'Donnell
as 1980's Fan
M.T
Meda Thomas
as 1980's Fan
J.A
Jack Andrade
as 1980's Fan
W.T
Warren Tashjian
as 1980's Fan
R.V
Ray 'Rocket' Valliere
as 1980's Fan
B.S
Bob Sands
as Landsdowne Street Fan
S.L
Stacey Lucchino
as Landsdowne Street Fan
A.N
Alison Novelli
as Landsdowne Street Fan
D.R
David Rosenberg
as Party Animal
J.P
Jesse Peter
as East Boston School Kid
Abe Farrelly
as East Boston School Kid
L.B
Lucy Bidwell
as East Boston School Kid
D
Docky
as Crazed Sox Fan
M.N
Mariann Neary
as Crazed Sox Fan
P.P
Paul Palandjian
as Fenway Security
Jeanne Zelasko
as Jeanne Zelasko
