Trailer
Cast
Jimmy Fallon
Ben Wrightman
KaDee Strickland
Robin
Sam Dissanayake
Mr. Abdo
Ione Skye
Molly
Mark Andrada
Ezra
Jackie Burroughs
Mrs. Warren
JoBeth Williams
Maureen Meeks
Jessamy Finet
Theresa
John Boylan
Myerson
Johnny Cicco
Bleacher Fan
Maureen Keiller
Viv
James B. Sikking
Doug Meeks
Charlotte Sullivan
Spin Instructor
Nicholas Purcell
Red Sox Fan (uncredited)
Jeanne Zelasko
Jeanne Zelasko
Marissa Jaret Winokur
Sarah
Scott Severance
Artie
Isabella Fink
Audrey
Greta Onieogou
Tammy
Willie Garson
Kevin
Zen Gesner
Steve
Andrew Wilson
Grant Wade
Scott Rosenberg
1980's Sox Player
Martin Roach
Husband
Andrea Davis
Wife
Matt Watts
Valet
Drew Barrymore
Lindsey Meeks
Brandon Craggs
Casey
Don Gavin
Cop
Brian Hayes Currie
Screaming Fan
Jack Kehler
Al
Daniel Greene
Waiter
Armando Riesco
Gerard
Siobhan Fallon Hogan
Lana
Evan Helmuth
Troy
Lenny Clarke
Uncle Carl
John Franchi
Red Sox Fan
Preston Thomas
1980's Sox Player
Abe Farrelly
East Boston School Kid
Johnny Sneed
Chris
Stephen King
Stephen King (uncredited)
Jason Spevack
Ben - 1980
Steve Levy
Reporter at Spring Training
Danny Murphy
1980's Vendor #1
Joe Buck
Sportscaster