Obba Babatundé as Tony

Charmin Lee White as Mrs. Tony Waters

Terrell Mitchell as Tony's Son

Enoh Essien as Tony's Daughter

Christopher Babers as Young Tony (as Chris Babers)

Jascha Washington as Young Alex

Drew Renkewitz as Prison Guard (as Drew Reukewitz)

Tim DeZarn as Guard Enheim

Hill Harper as Alex

Jennifer Freeman as Young Felicia (as Jennifer Nicole Freeman)

Hugh Dane as Mr. McDonald

Phylicia Rashād as Dr. Coles

Marla Gibbs as Lois Waters

Billy Dee Williams as Henry

Jordan Lund as Photographer

Efrain Figueroa as Parole Board Member Cruz

David Clennon as Parole Board Member Brenner

Talia Shire as Parole Board Member Marilyn

Glynn Turman as Parole Board Member Reingold

Amy Stiller as Parole Board Member Julie

Kirk Acevedo as Prospective Parolee

Rae Dawn Chong as Felicia

Baadja-Lyne Odums as Crack House Woman

Jaime Perry as Drug Dealer

David Roberson as Corrections Officer

Javier Silcock as Lamar

Jacin Guillienne Gayent Dixon as Guest at funeral (uncredited)

J.T. Thibodeau as Prison Guard (uncredited)