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)