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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