Madonna
Self

Erika Belle
Dancer (segment "Lucky Star") (segment "Papa Don't Preach")

Christopher Ciccone
Dancer (segment "Lucky Star")

John Leguizamo
Friend of Boyfriend (segment "Borderline")

Louie Louie
Boyfriend (segment "Borderline")

Deke Anderson
The Director (segment "Material Girl")

Keith Carradine
Boyfriend (segment "Material Girl")

Robert Wuhl
Pitch Man (segment "Material Girl")

Danny Aiello
Papa (segment "Papa Don't Preach")

Debi Mazar
Friend (segment "Papa Don't Preach")

Alex McArthur
Boyfriend (segment "Papa Don't Preach")

Mailon Rivera
Friend (segment "Papa Don't Preach")

Felix Howard
Kid (segment "Open Your Heart")

Benicio del Toro
Kid Sitting on Car (segment "La Isla Bonita")

Leon
Innocent Man / Saint (segment "Like a Prayer")

Cameron Alborzian
Man (segment "Express Yourself")

Todd Gordon
Factory Worker (segment "Express Yourself")

Gustav Vintas
Prison Wardon (segment "Express Yourself")

Tony Ward
Merman (segment "Cherish")

Mark Romano
Father (segment "Oh Father")