We start out with Madonna and a gang of friends all gathered round one of those areas where folks used to do spontaneous break-dancing back in the day, mainly because the Internet really hadn’t caught on just yet and people were bored. There’s a small child doing a backbend whilst Madonna, wearing trash-girl couture that was so popular back then, does some odd dance steps and then touches his hiney. In modern times, that would constitute child abuse and Madonna would get thrown in the Big House, but such overkill political correctness won’t happen for another twenty years or so.
Then we have a montage of street-dance sequences, where Madonna gets to show off the fact that she can throw her leg over her head, and we get introduced to her lover, a man-boy wearing tighter pants than she is. Everyone seems to be having a very good time, or at least as much fun as you can have when people are spinning around on their backs with their legs in the air, when some snooty photographer guy comes waltzing up and crashes the party without an invite.
Normally, this would require that one of the gang members get an attitude and pull a knife, but this isn’t reality, so the street folks just keep spinning and dancing unprofessionally while the photographer (let’s call him Hank) hands his business card to Madonna. We don’t know why Hank would single out Madonna, when most of the other folks are spinning and spreading their legs with much more gusto, so Hank must have a special fondness for the bandana thingy that Madonna has artfully woven through her hairdo that is bigger than Detroit.
Well, Man-Boy doesn’t care for small pieces of cardboard being handed to his lady-friend, and he makes a small scene that implies we don’t need no paparazzi up in here. (Apparently he doesn’t know Madonna very well, since she’s dreamed of paparazzi since the doctor slapped her newborn ass at the age of 10 seconds.) Madonna gives him a look (and a shove) that makes it clear that she and her bandana are going to do whatever it takes to not have to dance on this street corner any more.
Cut to Madonna hopping into Hank’s fancy car (while Man-Boy glares from what looks like a balcony in Barcelona, so there might have been some editing issues), and the next thing we know Madonna is wearing an outfit with extreme ruffles and screwing around with a giant ball while Hank takes pictures. (There’s also some business with Madonna wearing a leather jacket accented by a hairstyle jacked to Jesus, but it’s not clear if Hank is also recording that Madonna or if it’s just her auditioning for a Broadway revival of West Side Story.)
Next up are some shots of Madonna and Man-Boy on a rooftop somewhere. They seem to be very much in love, or at least horny, and they proceed to admire each other’s wardrobe and then make out. Zip back to Hank’s photography studio/penthouse, where now we have Madonna traipsing around in another leather outfit amongst some fake Greek columns and a giant statue of a naked man. Hank seems to be encouraging her to twirl as much as possible, when he really should be advising her to brush her hair at least once a week if she wants to be taken seriously.
Then we have a montage of Madonna in another frilly outfit that no serious person would ever wear unless under court order as she and Hank review the photos he has taken and they both guzzle margaritas. Apparently Madonna is quite pleased with Hank’s work, because she lustfully kisses him on the lips and they presumably proceed to have questionable sex while the giant naked statue reviews the proceedings.
Cut to a phone booth, with Madonna back in her street gear, a colorful ensemble with a Keith Haring theme and more hair that has not received proper attention. She’s hanging up on someone, but we don’t learn who it is because we have to see another round of Madonna dancing back at the studio. This turns into an extended scene where Madonna uses all of her acting skills to show that she can wear an outer garment that is clearly too big for her and maneuver her way through the Greek columns without mishap or any damage to the artwork.
Now we have Madonna (back in the Keith Haring outfit) standing on a street corner and chatting with several of her girlfriends, all of them sporting hairstyles courtesy of the Helen Keller Salon in SoHo. Man-Boy shows up and pouts whilst leaning against a lamppost and smoking a cigarette, because his part in the script wasn’t clearly defined and he’s winging it.
Madonna finally wanders over and tries to make nice, but her efforts are thwarted by Man-Boy doing something with an unexplained pool stick and his obvious dissatisfaction with her sluttiness (people talk, you know he’s got the 4-1-1 on her banging Hank and his foo-foo photography accessories) and the fact that her hair is bigger than his. He stomps away and heads back into a building, leaving Madonna to fret and kick the innocent lamppost, like it had anything to do with her bedding choices.
We go inside the building, where Man-Boy is playing pool (somewhat explaining the stick in the previous scene but not the manner in which he was fondling it), which is something some guys naturally do when their Former Squeeze is on the brink of international superstardom. Madonna appears in the doorway and tries to interest Man-Boy in her womanliness, or at least her more expensive couture, but he ignores her and keeps shoving balls into pockets. Madonna turns and struts away, apparently deciding that this is a part of her life that won’t make it into her autobiography anyway, so what’s the point?
Back to Hank’s studio, where Hank is smirking and Madonna is twirling, not showing any signs of guilt about working her way up the corporate ladder. Cut to Many-Boy walking up to a newsstand, surprising all of us that he reads, and seeing Madonna on the cover of “Gloss” magazine. He snatches up the magazine and proceeds to another Barcelona balcony so he can pout some more and have flashbacks of those special fifteen minutes that he and Madonna had on that random rooftop.
Studio once again, where Hank is trying to convince Madonna that she needs to wear an especially unattractive floppy hat for their next photo session. She doesn’t seem to care for it, but Hank gets her on his artistic-vision side by handing her a can of spray paint and letting her draw hearts on his fake marble wall. This appeals to she street side of Madonna, so she proceeds with the graffiti despite the stupid hat whilst Hank points and shoots.
Madonna, who firmly believes in excess, gets carried away and accidentally spray-paints Hank’s fancy car during the ecstatic exuberance of getting to deface property that does not belong to her. Hanks gets all pissy with Madonna, despite the obvious stupidity of Hank parking his car in the middle of a photo shoot, and there is an altercation, one that presumably does not lead to wanton sex.
Cut to Madonna waltzing down a darkened street, headed toward the pool hall where Man-Boy is still shoving a stick at balls and making it clear that he doesn’t have a real life or he wouldn’t still be there. First, Madonna greets her gal pals standing outside, because you always have to give props to your sisters or you get kicked out of the gang and you can’t have that kind of mess showing up in your autobiography, then she heads inside for the showdown with Stunted-Growth-Boy.
Madonna and the Pink Ladies sashay their way past Man-Boy, who apparently hasn’t moved from his position on the table since Oklahoma became a state, and then Madonna tries to appear disinterested as she peruses the selections on the jukebox. (After all, Joan Jett advised us years ago that we should put another dime in the jukebox, baby, and peer pressure is really hard to shake off despite counseling and distance from your formative years.)
Man-Boy rushes up to Madonna before she can insert anything into a slot, and they embrace each other fervently like Madonna didn’t offer her wares to the first guy who had more than just liability insurance on his car. To confirm their back-togetherness, we cut to Man-Boy showing Madonna just exactly how his pool stick should be handled to achieve the most satisfaction. We finish out with another shot of Madonna singing the final notes of the song and wearing that ill-advised floppy hat with the most annoying bow known to mankind…
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