 MadonnaSelf | Self |
 Tomas AranaStranger (segment "Bad Girl") | Stranger (segment "Bad Girl") |
 Rob CampbellStranger (segment "Bad Girl") | Stranger (segment "Bad Girl") |
 Matt DillonDetective (segment "Bad Girl") | Detective (segment "Bad Girl") |
 Jamie KingDancer (segment "Human Nature") | Dancer (segment "Human Nature") |
 Mark MargolisBartender (segment "Bad Girl") | Bartender (segment "Bad Girl") |
| EEmilio MuñozTorero (segment "Take a Bow") | Torero (segment "Take a Bow") |
 Mike MyersAustin Powers (segment "Beautiful Stranger") | Austin Powers (segment "Beautiful Stranger") |
| RRika OharaWardrobe Girl (segment "Rain") | Wardrobe Girl (segment "Rain") |
 Jason OliveLover (segment "Secret") | Lover (segment "Secret") |
 Anita Pallenberg(segment "Drowned World / Substitute for Love") | (segment "Drowned World / Substitute for Love") |
 James RebhornStranger (segment "Bad Girl") | Stranger (segment "Bad Girl") |
 Daniel Louis RivasKid Sitting on Stairs (segment "Secret") | Kid Sitting on Stairs (segment "Secret") |
 Ryuichi SakamotoDirector (segment "Rain") | Director (segment "Rain") |
 Jenny ShimizuProduction Assistant Girl (segment "Rain") | Production Assistant Girl (segment "Rain") |
| SSam SpiegelRecord Producer (segment "Drowned World / Substitute for Love") | Record Producer (segment "Drowned World / Substitute for Love") |
 Steve Strange(segment "Drowned World / Substitute for Love") | (segment "Drowned World / Substitute for Love") |
| RRuth TaverasDancer (segment "Human Nature") | Dancer (segment "Human Nature") |
 Luca TommassiniDancer (segment "Human Nature") | Dancer (segment "Human Nature") |
 Verne TroyerMini-Me (segment "Beautiful Stranger") | Mini-Me (segment "Beautiful Stranger") |
 Goran VišnjićBoyfriend (segment "The Power of Good-bye") | Boyfriend (segment "The Power of Good-bye") |
 Christopher WalkenGuardian Angel (segment "Bad Girl") (archive footage) | Guardian Angel (segment "Bad Girl") (archive footage) |
 Michael Kenneth Williams(segment "Secret") | (segment "Secret") |
 Michael YorkBasil Exposition (segment "Beautiful Stranger") | Basil Exposition (segment "Beautiful Stranger") |
