

05/11/1999
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.

Chris O'Donnell
as Jimmie

Renée Zellweger
as Anne

Artie Lange
as Marco

Ed Asner
as Gluckman

Hal Holbrook
as O'Dell

James Cromwell
as Priest

Marley Shelton
as Natalie

Peter Ustinov
as Grandad

Katharine Towne
as Monique

Rebecca Cross
as Stacey

Stacy Edwards
as Zoe

Mariah Carey
as Ilana

Sarah Silverman
as Carolyn

Jennifer Esposito
as Daphne

Brooke Shields
as Buckley

Lydell M. Cheshier
as Sanzel

Robert Kotecki
as Hodgman

Pat Finn
as Bolt

Tim Perez
as Stone

Romy Rosemont
as Rita

Kelly Jean Peters
as Waitress

Jane L. Powell
as Starlight Room Singer

Jim Jackman
as Nervous Guy

Christopher Carroll
as Maitre d'

Kevin Jones
as Florist

Michael Deeg
as Customer

Erik Kever Ryle
as Customer

Brian Leonard
as Customer

Mary J. White
as Florist Assistant

Edith Fields
as Edith

Joe Meek
as Trader

Michael Lee Merrins
as Trader

Lisa Nalen
as 'Anne' on the Street

Brantley Bush
as Stagehand

Nicholas Pryor
as Dale

Maree Cheatham
as Mona

Mark Norby
as Suspect

Ken Baldwin
as Salsa Dancer

Gustavo Vargas
as Salsa Dancer

Natalie Bartlett
as O'Dell's Daughter

Cheri Rae Russell
as Biker Bride

Jodi Taylor
as Older Bride

Jenni Pulos
as Big Hair Bride

Rebecca Gray
as Punk Bride

Kiva Dawson
as Punk Bride

Anastasia Horne
as Preppy Bride

Niecy Nash-Betts
as African-American Bride

T.L. Brooke
as Big Bride

Marnie Alexenburg
as Brunette Bride

Lea Moon Llovio
as Latina Bride

Robin Lyon
as Questioning Bride

Elizabeth Guber
as Questioning Bride

Nancy O'Dell
as Questioning Bride

Marnie Schneider
as Muslim Bride

Louis Ganapoler
as Baker

Chace Acton
as Girl on Swing (uncredited)

Andy Arness
as Businessman (uncredited)

Jeffrey J. Ayers
as Trader (uncredited)

Jason Aaron Baca
as Groomsman #3 (uncredited)

Annie Coffey
as Bride (uncredited)

Tracey Evans
as Questioning Bride (uncredited)

Steve Hosford
as Trader (uncredited)

Johnny Liska
as Newsstand Vendor (uncredited)

Jen McAllister
as Bride in Subway (uncredited)

Amy Mills
as Questioning Bride (uncredited)

Shenita Moore
as Afro Bride (uncredited)

Cal Nguyen
as Pedestrian (uncredited)

Johan-Carl Nowack
as Groomsman (uncredited)

Scott Trimble
as Stockbroker (uncredited)
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