
101 minutes
11/5/1999
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)