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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
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 she wanted. We talked about wanting to tap into a working-class environment, because by that time she had done "Material Girl" and "Like a Virgin" and other stuff that was very glamorous and stylized. She wanted to do something a bit more grounded and "drama." I said, "You know a great place to shoot is Staten Island in New York." She said, "Why?" I said, "Well, I grew up there, and If I go back and make a video there with you, then I'll be the conquering hero and all my friends from high school can see what I've accomplished." It turned out to actually be the case. [Laughs]

We took the script literally from the lyrics of the song, and I remember having a moment's hesitation about doing that because most videos are not literal interpretations. But I just felt like it was something that tied into her desire to dip into the working-class world. I did have the idea that there should be a segment of the video where she was Madonna — not the character in the story — and that's where it cuts to the black and white stuff of her dancing around for the chorus.

I wanted to do a scene on the Staten Island Ferry just because it was such a big part of my growing up. We had to rent the ferry for the night and we finished early and had a couple of hours left. The captain said, "Well, you own it for the next two hours. Do you want to go anywhere?" So me, the crew and her just drove around the harbor to places that I had never seen in my life. It was a magical memory.

It was her idea to cast Danny Aiello as her father. She was just so blazingly hot that anybody involved felt very excited and happy. When we were shooting in Staten Island, there were thousands of people and paparazzi and everything. The whole thing had the air of a pleasurable circus to it and Danny just played right into that. A couple weeks after the video was released and was a huge hit, he recorded an answer song called "Papa Wants the Best for You." He has an incredible, booming voice, but it was a ludicrous song. He called me up and wanted her to be in his video and said, "She owes me this." That didn't go very far.

I've made a bunch of films and videos and it's one of the five things that I've done that I feel unequivocally good about. The strongest thing I came away from was the value of creative freedom, and that she used that in a very smart way. She's extremely focused and mature and had a work ethic. It was a good lesson to me: what to do with absolute, creative power. She's respectful of people's jobs and sees herself where she fits into it very well. I always thought, whenever I get total