Drew Barrymore (Lindsey)
Jimmy Fallon (Ben)
Jason Spevack (Ben (1980))
Jack Kehler (Al)
Scott H. Severance (Artie)
Matt Watts (Valet)
Andrea Davis (Wife)
Sharlene Yuen (Receptionist)
Geoffrey Williamson (High School Kid #1)
Jim Rice (Himself)
Dennis Eckersley (Himself)
Ken Rogerson (Scalper)
Paul Mcguire (Reporter)
Trot Nixon (Himself)
Johnny Damon (Himself)
Jason Varitek (Himself)
Bobby Curcuro (Loiterer)
Gina Clayton (Lady At Other Table)
Dan Darin-Zanco (Husband)
Keith Macwhorter (Himself)
Melinda Lopez (Sheri)
Sam Dissanayake (Mr. Abdo)
George King (Mr. Munsell)
Jordan Leandre (Himself)
Dan Cummings (1980's Vendor #2)
John Ruggiero (Hot Dog Vendor #2)
Bob Weekes (Hot Dog Vendor #1)
Brian Hayes Currie (Screaming Fan)
Johnny Cicco (Obnoxious Fan)
Erin Nanstad (Female Fan)
Jermaine Plummer (High School Kid #4)
David Klar (High School Kid #3)
Matthew Peart (High School Kid #2)
Harold Reynolds (Himself)
Don Orsillo (Himself)
Steve Levy (Reporter At Spring Training)
Don Gavin (Cop)
Shary Guthrie (Christie)
Lizz Alexander (Charlene)
John Boylan (Myerson)
George Ghali (Vern (gym Teacher))
Miranda Black (Carrie)
Marissa Jaret Winokur (Sarah)
Johnny Sneed (Chris)
Danny Murphy (1980's Vendor #1)
Charlotte Sullivan (Spin Instructor)
Zen Gesner (Steve)
Andrew Wilson (Grant Wade)
Wayne Fleming (Leon)
JoBeth Williams (Maureen Meeks)
James B. Sikking (Doug Meeks)
Tim McCarver (Himself)
Daniel Greene (Waiter)
Willie Garson (Kevin)
Siobhan Fallon-Hogan (Lana)
Quancetia Hamilton (Rita)
Jackie Burroughs (Mrs. Warren)
Scott Desano (Binocular Guy)
Mark Andrada (Ezra)
Greta Onieogou (Tammy)
Isabella Fink (Audrey)
Brett Murphy (Ryan)
Brandon Craggs (Casey)
Howard Nickerson (Usher)
Michael Rubenfeld (Ian)
Armando Riesco (Gerard)
J. C. Kenny (Reporter)
Darren Frost (Zach)
Peter Gammons (Himself)
Evan Helmuth (Troy)
Bart Bedford (Man At Other Table)
KaDee Strickland (Robin)
Jessamy R. Finét (Teresa)
Maureen Keiller (Viv)
Lenny Clarke (Uncle Carl)
Ione Skye (Molly)