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Express Yourself: The Making of Madonna’s 20 Greatest Music Videos

The directors who worked alongside the MTV-era maverick tell their stories

Madonna

Since first storming MTV in 1983 with the poetic, lo-fi "Burning Up," Madonna's music videos have spent more than 20 years sparking conversations about fashion, feminism, sex, religion and what you could and could not show on television. To help her realize these 67 clips — one of the most rapidly changing visions in pop history — she teamed up with some video and photography's most celebrated artists, including David Fincher, Jean-Baptiste Mondino, Herb Ritts, Mark Romanek, Chris Cunningham, Stéphane Sednaoui, Jonas Åkerlund, Luc Besson and more.

"Madonna was the one you had to get," says Michael Hausmann, director of her mid-Nineties clips for "Take a Bow" and "You'll See." "That was the video that would be the most airtime. It was, in some ways, kind of more important than having a movie out. More people were watching it, that’s for damn sure."

To celebrate our cover star, we caught up with many of the directors behind some of the most iconic (and controversial) images in music history.

Madonna
12

“Justify My Love” (1990)

"When I did my 'Vogue' video'…I'm wearing a see-through dress and you can clearly see my breasts," Madonna told ABC's Nightline in 1990. "Now, [MTV] told me that they wanted me to take that out, but I said I wouldn't and they played it anyways. So I thought that once again I was going to be able to bend the rules a little bit." She was definitely wrong. The Jean-Baptiste Mondino-directed clip for "Justify My Love" toyed with S&M, group sex and even some bare-breasts in an outfit reminiscent of Nazisploitation flick The Night Porter — but all filmed with a gorgeous, gauzy, dreamlike black-and-white Euro art-house vibe. "We respect her work as an artist and think she makes great videos," said MTV executives in a statement about the clip. "This one is not for us." The resourceful Madonna spun the controversy into the best-selling "video single" of all time. "You know, she's a very clever woman and she said nothing could stop it," says Mondino. "I remember, at Tower Records, there were piles of the video being on sale. So, she even made money off with it — so it's brilliant."

Jean-Baptiste Mondino, director: That video was very special. That song was very, very progressive, very unusual. It was Lenny Kravitz who wrote it, he was singing, but he was almost talking, and he had that strange beat. You couldn't really dance to it. It was all whispering — it sounds more like an experience. Nobody would pick up a song like this and try to make a hit out of it, don't you think so? So it forces me—or it seduced me, in that sense—to be as courageous as the song is.

In fact what I did with that video, I did an experience. The whole idea was to lock ourselves into this hotel for three days and two nights. Without out any rules. We rent the whole top floor of that hotel. You know usually when you do a shoot, you have timing… So we didn't have none of this. This is the rooms that we were sleeping in, living in. Maybe 15 rooms. One room was [the] makeup room, one was the wardrobe. Nobody was allowed to go out. There were tables with food in it, and when people were starving, they were eating. There were no rules — we had alcohol, we could smoke. 

I didn't have any concept at all, except the idea that she was arriving in the hotel tired, broken; and when she was going to leave the hotel, she was full of life, she was full of energy, full of everything. It was a very strange experience; very interesting. For instance, the cinematographer, we said, "We're not going to use anything like we use usually when we shoot….It was very strange because we didn't know when we were doing the film or when it was real, you know? The whole thing was mixed up. The last morning when I woke up and had to go back home, I felt very strange on the sidewalk. I said, "Do I have to go home or not?" It was the first time in my life I didn't know what to do, because I had like a dream — it was not a shoot. You could tell that some of the scenes, they smell real. There's something about it. Things were just happening.

When are you free like this, you don't become savage — you become even more nicer. If you go to a sex club, where people are making sex, you would see less tension than you would get if you go in a normal club. There's less frustration. So it was very quiet, it was very gentle, we were all very sweet to each other….It was not like, "Madonna has a certain treatment" where you couldn't talk to her. She was very comfortable with people around. We were talking, chatting, laughing, playing the music, shooting and when people were tired they went to bed. That's all….Maybe there is more behind-the-scenes story to tell when you see a normal video [laughs].

Honestly, I was surprised that that video was that shocking because we don't see anything: We don't see any pubes hair, we don't see any tits almost, they don't do anything wrong. We're all here on Earth because our parents they make sex, right? So, I don't get it. I mean, porn for me is when people are killing each other. You go to see a movie, we see blood everywhere, but we never see a dick or a pair of tits. We are here because people fuck, so, we should be proud of the fucking thing.

Madonna
11

“Material Girl” (1985)

"Marilyn was made into something not human in a way, and I can relate to that," said Madonna. "Her sexuality was something everyone was obsessed with, and that I can relate to. And there were certain things about her vulnerability that I'm curious about and attracted to." This homage to Marilyn Monroe's 1953 film Gentlemen Prefer Blondes probably ended up being homaged even more than the original: Taylor Swift's recent performance of "Shake it Off" at the 2014 MTV Video Music Awards may have been more Madge than Norma Jean. (Says director Mary Lambert of Swift, "I think she's amazing and I was flattered"). Though Madonna would soon venture into movies like Vision Quest, Desperately Seeking Susan and Who's That Girl, "Material Girl" was shot like a stand alone film with a music video it its core: the Hollywood backlot exteriors looking cinematic, the "stage" interiors glossy and fun. Her cadre of tuxedo'd dancers took their share of choreographed slaps and spills on camera, but no one was hurt. "And anyway," says Lambert, "they were all so infatuated with Madonna, they wouldn't have felt a thing.

Mary Lambert, director: I have always been extremely interested in Marilyn Monroe — her life and persona. Madonna and I shared that fascination. I watched the dance sequence from Gentlemen Prefer Blondes about a million times with [choreographer] Kenny Ortega, who brilliantly reinterpreted it for the film. "Material Girl" was my first collaboration with costume designer Marlene Stewart, who brilliantly reinterpreted the dress. If you have a very specific vision in mind, work with talented people, that's my advice.

Madonna
10

“Cherish” (1989)

The photographer Herb Ritts and Madonna struck up a friendship early in Madonna's career, with Ritts shooting the glammed-out cover for the 1986 album True Blue and photographs for Rolling Stone — including the cover for the September 10, 1987 issue. But what Madonna really wanted Ritts to do was direct. "She kept asking me, and I said I really didn't know the first thing about moving imagery," Ritts told the art curator François Quintin in a 1999 interview. "Finally, I practiced with a little Super 8 camera when I was on a job in Hawaii, and came back and said I could do it. Two weeks later, I was filming 'Cherish.' I directed it and did the camera work as well. It was invigorating." Madonna was pretty invigorated by the black-and-white, mermen-filled shoot as well: "I made her dive into the freezing ocean. She was a real trooper," the late Ritts told the Toronto Star in 1990. The playful video became an MTV staple, a light jaunt on the beach after the controversy-drenched "Like A Prayer" and the future-shocked "Express Yourself." Ritts went back to the beach when he directed the videos for Janet Jackson's joyful "Love Will Never Do (Without You)" and Chris Isaak's brooding "Wicked Game."

Madonna
9

“Like a Virgin” (1984)

"By that point Madonna was on the cover of Rolling Stone," Warner Bros. creative director Jeff Ayeroff said in I Want My MTV. "So we went to Venice, like a bunch of fucking whack jobs. I don't know what we spent — $150,000? $175,000? — but it was way more than we'd ever spent on a video." For their second collaboration (after 1984's "Borderline") director Mary Lambert shot the pop star on gondolas in Venetian canals (with Ayeroff telling her to duck when the bridges approached). A man in a lion's mask stalked her like prey, but an actual lion ended up stealing the spotlight.

Mary Lambert, director: This was the first time I worked with a big cat, although I've worked with them since. It wasn't even a trained lion! The local line producer made a deal with a guy from the circus. It was a circus lion! I didn't find this out until Madonna and the cinematographer and I were alone in a fenced off area with the animal and the trainer was standing on the perimeter with a rifle, "Just in case"…. At one point the lion started sniffing Madonna's crotch and I thought she might be a goner.

Madonna
8

“Vogue” (1990)

Madonna's third collaboration with then-wunderkind David Fincher is an eye-popping kaleidoscope of classic movie star iconography and an energetic display of the titular dance which had emerged in the underground gay club scene. Of course, voguing is no ordinary dance, consisting as it does of highly mannered movements, baroque hand gestures and sharply struck poses — the catwalk ethos taken to absurdist extremes. That gives Fincher's camera the chance to move elegantly around statues, paintings and frozen, statuesque humans, bringing out the curious melancholy undercurrent to a song that, at first listen, seems like pure bubblegum. Watch the infectious way the video develops – from unsettling stillness to sinewy movements to full-on dance freakout. It's structured like a vogue dance itself. (And, really, did anyone shoot Madonna's back better than David Fincher?)

Remarkably, this iconic video was prepared in record time, as the song was not originally considered a single and was only belatedly put out into the market. "We cut this thing together as quickly as we could," recalled Fincher to The Guardian. "It was one of those things where the DP, Pascal Lebegue, who's brilliant, literally showed up off the plane with his light meter and it was semi-pre-lit and he walked in and said, 'This, this, this, this,' and we shot the video for like 16 hours and we were done, that was it, she got on the plane and went on her world tour." 

Madonna had quickly auditioned hundreds of dancers in Los Angeles for the clip, whittling them down within a matter of days and inviting them out to clubs to make sure they could deliver. "I'd just finished ballet school, and this was my second video," dancer Salim "Slam" Gauwloos said. "I remember David said, 'Put him in this tuxedo jacket. So I wore that, and they put me on some steps, and I was doing some poses, and it took like 15 minutes, and I was like, 'OK, is that it?' I thought, This is not a good beginning. But then when the 'Vogue' video came out, I was like, 'Ah OK! Now I get it!'"

Madonna
7

“Papa Don’t Preach” (1986)

"Papa Don't Preach" finds Madonna treating the music video concept as more of a short film than promotional clip, imbuing her character — a teenager who discloses an unplanned pregnancy to her strict father (played by Danny Aiello) — with a mature, sympathetic tone far removed from her sex-symbol image. Shot over three days in Staten Island and Manhattan, director James Foley says that despite the seriousness of the song, the vibe was "pure fun." "No one was getting down about the message or social importance of it," he says. "We just liked to blast it as loud as possible."

James Foley, director: I was a bit spoiled because she had absolute creative freedom and could do whatever