Cameron Diaz ... Mary
Matt Dillon ... Healy
Ben Stiller ... Ted
Lee Evans ... Tucker
Chris Elliott ... Dom
Lin Shaye ... Magda
Jeffrey Tambor ... Sully
Markie Post ... Mary's Mom
Keith David ... Mary's Dad
W. Earl Brown ... Warren
Sarah Silverman ... Brenda
Khandi Alexander ... Joanie
Marnie Alexenburg ... Lisa
Danny Murphy ... Boss' Brother (as Dan Murphy)
Richard Tyson ... Detective Krevoy (as Richard M. Tyson)
Rob Moran ... Detective Stabler
Jackie Flynn ... South Carolina Police
Hillary Matthews ... Dom's Wife
Willie Garson ... Dr. Zit Face / High School Pal
David Shackelford ... Coconut Guy
David Goryl ... Petey
Lori Brener ... Friend #3 (as Lori Glick)
Jeffrey P. Lerner ... Car Hood Kid #1
Cory Pendergast ... Car Hood Kid #2
Brett Favre ... Himself
Warren Tashjian ... Freddie
Kelly Roarke ... Girl
Herbie Flynn ... Homeless Man
Caryl West ... Medical Assistant #1
Ken Rogerson ... Pants at Ankles Guy
Brad Blank ... Paramedic
Steve Sweeney ... Police Officer
Cindy Oliver ... Renise
Will Coogan ... Smokey
Steve Tyler ... TV News Reporter
Maureen Griffin ... Wine Waitress
Docky ... Hot Dog Stud (as The Artist Formerly Known As Docky)
Mariann Farrelly ... Driving Range Sweetie
Jonathan Richman ... Jonathan
Tommy Larkins ... Drummer
Lenny Clarke ... Fireman
Daniel Greene ... Pizza House Man (scenes deleted)
Michael Budge ... Joey Bishop Look-alike
James Gifford ... Jimmy
Sean Gildea ... Prison Warden (as Sean P. Gildea)
Zen Gesner ... Bartender
Tracy Anne George ... Dancer
Jesse Farrelly ... Dom's Kid (as Jesse)
Anna Farrelly ... Dom's Kid
Zack Lee ... Mary's Little Friend
Valerie Bruce ... Nimrod's Cafe Patron
Kelly O'Brien ... Office Assistant
Mike Charpentier ... Hot Club Patron
Peter Grundy ... Hot Club Patron
Michael 'The Cannon' Gannon ... Hot Club Patron (as Michael Gannon)
Peter Conway ... Hot Club Patron
Ann Conway ... Hot Club Patron
Susan O'Day ... Hot Club Patron
Heather Rosbeck ... Hot Club Patron
Jack Shields ... Hot Club Barkeep
Fallon Shields ... Hot Club Barkeep
Bob Grundy ... Hot Club Barkeep
Nancy Farrelly ... Boardroom Babe
Bill Beauchene ... Insurance Spitballer (as Billy Beauchene)
Kathy Beauchene ... Insurance Spitballer
Manny Barrows ... Insurance Spitballer
Michael Murphy ... Office Worker
Sheila Mone ... Office Worker
Barbara O'Connor ... Ashtray Babe
Tim Sheehan ... Camera Hog
Richie Balsbaugh ... Cigar Smoker
Jim Blake ... Architect Partier (as Jim "Sunshine" Blake)
Tim Robbie ... Architect Partier
Providence Wissel ... Architect Partier
Ruth Michelle Meyer ... Architect Partier
Billy Meyer ... Architect Partier
Brian McGlaughlin ... Architect Partier
Brian Mone ... Architect Partier
John Stroehman ... Architect Partier
Pete Anicelli ... Architect Partier
Duana Knight ... Architect Babe
Kelley Schneider ... Architect Babe
Meda Thomas ... Architect Babe
Steve ... Rest Stop Couple
Kenny ... Rest Stop Couple
Pat ... Rest Stop Couple
Mike ... Rest Stop Couple
Billy Dee ... Rest Stop Couple (as Larry)
Sam ... Rest Stop Couple
Ernie ... Rest Stop Couple
Tom ... Rest Stop Couple
Chris ... Rest Stop Couple
Rosie ... Rest Stop Couple
Jeanie Flynn ... Cuban Dancer
Kevin Civale ... Cuban Dancer (as Kevin Civali)
Tom Leasca ... Cuban Dancer
Mercy Lopez ... Cuban Dancer
Michael Cheney ... Cell Block Bitch
Scott Rosenberg ... Jailbird
George Bedard ... Jailbird
Terry Mullany ... Jailbird
Rick Coleman ... Jailbird
Michael Burke ... Jailbird
Kris Meyer ... Jailbird
Emilio Diaz ... Jailbird
Billy Smith ... Jailbird
Ed Nelson ... Jailbird
Brian Stube ... Jailbird
Don Daley ... Jailbird
Clem Franek ... Strip Club Pervert
Julia Hissom ... Strip Club Pervert
James 'Sporty' Ahern ... Strip Club Pervert (as Sport Ahern)
Robin Gau ... Strip Club Pervert
Paul Pelletier ... Cordosa Gawker (as Paul)
Monique Pelletier ... Cordosa Gawker
Jon Mone ... Comic Book Kid (as Johnny Mone)
Nicholas Greenbury ... Fish Hook Kid (as Nick)
Andrew Greenbury ... Fish Hook Kid
Phil Rosenberg ... Cell Block Masseuse
John-Eliot Jordan ... Buttercup Singer
John Adamonis ... Buttercup Singer
Kyle Adamonis ... Buttercup Singer
Neil Pomfret ... Buttercup Singer
Ruth Pomfret ... Buttercup Singer
Josh Miller ... Buttercup Singer
Deborah Smith Ford ... Doctor (uncredited)
Debbie Howard ... Tourist (uncredited)
Richard Jenkins ... Psychiatrist (uncredited)
Don Julio ... Jailbird (uncredited)
Rick Michaels ... Restaurant Waiter (uncredited)
Cord Newman ... Extra (uncredited)
Al Quinn ... Domino Player (uncredited)
Harland Williams ... Hitchhiker (uncredited)

Ted was a geek in high school, who was going to go to the prom with one of the most popular girls in school, Mary. The prom date never happened, because Ted had a very unusual accident. Thirteen years later he realizes he is still in love with Mary, so he hires a private investigator to track her down. That investigator discovers he too may be in love with Mary, so he gives Ted some false information to keep him away from her. But soon Ted finds himself back into Mary's life, as we watch one funny scene after another.

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