Madonna as Self

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

Christopher Ciccone as Dancer (segment "Lucky Star")

John Leguizamo as Friend of Boyfriend (segment "Borderline")

Louie Louie as Boyfriend (segment "Borderline")

Deke Anderson as The Director (segment "Material Girl")

Keith Carradine as Boyfriend (segment "Material Girl")

Sharon Oreck as Woman in clown costume (segment "Material Girl")

Robert Wuhl as Pitch Man (segment "Material Girl")

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

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

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

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

Felix Howard as Kid (segment "Open Your Heart")

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

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

Cameron Alborzian as Man (segment "Express Yourself")

Todd Gordon as Factory Worker (segment "Express Yourself")

Gustav Vintas as Prison Wardon (segment "Express Yourself")

Tony Ward as Merman (segment "Cherish")

Mark Romano as Father (segment "Oh Father")

Luis Camacho as Voguer (segment "Vogue")

Oliver Crumes Jr. as Voguer (segment "Vogue")

Donna DeLory as Voguer (segment "Vogue")

Salim Gauwloos as Voguer (segment "Vogue")

Jose Guitierez as Voguer (segment "Vogue")

Niki Haris as Voguer (segment "Vogue")

Kevin Stea as Voguer (segment "Vogue")

Gabriel Trupin as Voguer (segment "Vogue")

Carlton Wilborn as Voguer (segment "Vogue")