
1998
Sometimes you have to break the rules to free your heart.
Through good times and bad, Stella and Delilah have always had each other. Now, Stella's so busy building a life that she's forgotten how to really live. But Delilah is about to change all that. What starts as a quick trip to Jamaica, ends as an exhilarating voyage of self discovery as Stella learns to open her heart and find love – even if it's with a man 20 years her junior.

Angela Bassett
Stella Payne

Taye Diggs
Winston Shakespeare

Whoopi Goldberg
Delilah Abraham

Regina King
Vanessa

Suzzanne Douglas
Angela

Michael J. Pagan
Quincy Payne

Sicily Johnson
Chantel

Richard Lawson
Jack

Barry Shabaka Henley
Buddy

Lee Weaver
Nate

Glynn Turman
Dr. Shakespeare

Phyllis Yvonne Stickney
Mrs. Shakespeare

Denise Hunt
Ms. Thang

Lisa Hanna
Abby

James Pickens Jr.
Walter Payne

Philip Casnoff
Kennedy

Lou Myers
Uncle Ollie

D'Army Bailey
Minister

Art Metrano
Dr. Steinberg

Carl Lumbly
Judge Spencer Boyle

Phina Oruche
Leslie James

Tenny Miller
Kitchen Worker

Andrew Palmer
Buffet Server

Harold Dawkins
Upbeaters Band

Kenneth Buckford
Upbeaters Band

Simon Street
Upbeaters Band

Craig Blake
Winston's Friend

Elisabeth Granli
Girl in Jamaica Commercial

Steve Danton
Man in Commercial

Elly McGuire
Stella's Friend

Selma McPherson
Friend at Party #1

Fern Ward
Friend at Party #2

Lucinda Chrisman
Moviegoer (uncredited)

Leroy Edwards III
Dreadlocked Man in Commercial (uncredited)

Victor Garber
Isaac (uncredited)

David C. Waite
Guy by pool / Pajama Party Guest (uncredited)

Zaina Juliette
Stella Body Double

Over the Fence

Nice View

The 'Burbs

Caddyshack

Legendary Panty Mask

Miracle on 34th Street

The Sweetest Thing

Alone Among Women

Mamma Mia!

Nonnas

Suburban Girl

My Sweetheart Wants to Go Sailing on Sunday

In Space with Markiplier: Part 2

A Muppet Family Christmas

Chill Out, Scooby-Doo!

Ice Princess

Kes

Please, ̶D̶o̶n̶'̶t̶ Stay

Son of Rambow

Scarlett