
The Bachelor
Jimmie is seeing his single friends get married one by one. He isn't too worried until his girlfriend Anne catches the bouquet at his friend Marco's wedding. Suddenly, his wild mustang days are numbered. He finally decides to propose to her, but he sticks his foot in his mouth and botches the proposal. Being insulted by the defeatist proposal, Anne leaves town on an assignment. After she's gone, he finds out that his recently-deceased grandfather's will stipulates that he gets nothing of a multi-million dollar fortune unless he's married by 6:05pm on his 30th birthday: tomorrow! Not being able to find Anne, Jimmie begins backtracking through his past girlfriends to find a wife.
The Bachelor
November 5, 1999
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Cast (69)

Chris O'Donnell
Jimmie

Renée Zellweger
Anne

Artie Lange
Marco

Ed Asner
Gluckman

Hal Holbrook
O'Dell

James Cromwell
Priest

Marley Shelton
Natalie

Peter Ustinov
Grandad

Katharine Towne
Monique

Rebecca Cross
Stacey

Stacy Edwards
Zoe

Mariah Carey
Ilana

Sarah Silverman
Carolyn

Jennifer Esposito
Daphne

Brooke Shields
Buckley

Lydell M. Cheshier
Sanzel

Robert Kotecki
Hodgman

Pat Finn
Bolt

Tim Perez
Stone

Romy Rosemont
Rita

Kelly Jean Peters
Waitress

Jane L. Powell
Starlight Room Singer

Jim Jackman
Nervous Guy

Christopher Carroll
Maitre d'

Kevin Jones
Florist

Michael Deeg
Customer

Erik Kever Ryle
Customer

Brian Leonard
Customer

Mary J. White
Florist Assistant

Edith Fields
Edith

Joe Meek
Trader

Michael Lee Merrins
Trader

Lisa Nalen
'Anne' on the Street

Brantley Bush
Stagehand

Nicholas Pryor
Dale

Maree Cheatham
Mona

Mark Norby
Suspect

Ken Baldwin
Salsa Dancer

Gustavo Vargas
Salsa Dancer

Natalie Bartlett
O'Dell's Daughter

Cheri Rae Russell
Biker Bride

Jodi Taylor
Older Bride

Jenni Pulos
Big Hair Bride

Rebecca Gray
Punk Bride

Kiva Dawson
Punk Bride

Anastasia Horne
Preppy Bride

Niecy Nash-Betts
African-American Bride

T.L. Brooke
Big Bride

Marnie Alexenburg
Brunette Bride

Lea Moon Llovio
Latina Bride

Robin Lyon
Questioning Bride

Elizabeth Guber
Questioning Bride

Nancy O'Dell
Questioning Bride

Marnie Schneider
Muslim Bride

Louis Ganapoler
Baker

Chace Acton
Girl on Swing (uncredited)

Andy Arness
Businessman (uncredited)

Jeffrey J. Ayers
Trader (uncredited)

Jason Aaron Baca
Groomsman #3 (uncredited)

Annie Coffey
Bride (uncredited)

Tracey Evans
Questioning Bride (uncredited)

Steve Hosford
Trader (uncredited)

Johnny Liska
Newsstand Vendor (uncredited)

Jen McAllister
Bride in Subway (uncredited)

Amy Mills
Questioning Bride (uncredited)

Shenita Moore
Afro Bride (uncredited)

Cal Nguyen
Pedestrian (uncredited)

Johan-Carl Nowack
Groomsman (uncredited)

Scott Trimble
Stockbroker (uncredited)
Crew (24)
Directing

Gary Sinyor
Director
Writing

Steve Cohen
Screenplay

Roi Cooper Megrue
Theatre Play
Production

Chris O'Donnell
Executive Producer

Michael De Luca
Executive Producer

Lloyd Segan
Producer

Valerie McCaffrey
Casting

Jeffrey T. Barabe
Producer

Bing Howenstein
Producer

Gene Levy
Line Producer

Leon Dudevoir
Co-Producer

Stephen W. Hollocker
Co-Producer

Donna Langley
Executive Producer
Sound
Art
Camera

Simon Archer
Director of Photography
Costume & Make-Up

Terry Dresbach
Costume Design
Crew

Merritt Yohnka
Stunts

Tony R. Medina
Propmaker
Editing

Robert M. Reitano
Editor