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The Making of Madonna’s 20 Greatest Music Videos

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

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.

20. “Hung Up” (2005)

Weeks before Madonna was scheduled to shoot the clip for the ABBA-borrowing lead single from Confessions on a Dance Floor, she had a horseback-riding mishap that resulted in her breaking eight bones. This didn’t deter her from turning her section of the “Hung Up” video into a John Travolta homage. Wearing a long-sleeved pink leotard, she danced around a rehearsal studio with gusto in scenes culled from a three-hour shoot in which she had to frequently take breaks because she was in pain. “She was such a trooper,” director Jonah Renck (a last-minute stand-in for David LaChapelle) told MTV News in 2006. “She just fell off a horse!” The rest of the video pays tribute to the idea of music as a unifying force, with restaurant employees, bus-stop congregants and parkour enthusiasts grooving to the sinuous track. “I kind of liked that we didn’t have time to overthink this and be too clever,” Renck said. “I like being out on a limb and not know what we’re doing and why. Just deal with it, the mayhem, you know?”

19. “Fever” (1993)

“The idea came that I wanted, basically, to burn her,” says director Stéphane Sednaoui. “My concept was that she was kind of Joan of Arc. I wanted her like a provocative saint, somebody that speaks out and tells the truth, and is ready to burn for it. I remember the big boss at Maverick — [Madonna] was the big boss, but she had somebody else with her — was really worried that I would burn her. He thought it was a very negative image for her.” While Madonna doesn’t catch on fire in the clip (“she was more like…incandescent?” says Sednaoui), after a two-day shoot in Miami, she was run through a gauntlet of hallucinogenic, high-contrast post-production from the eye-searing director of the Chili Peppers’ “Give it Away” and U2’s “Mysterious Ways.” The clip — full of dizzying zooms — bursts with color, from her red wig, to her gold dress, to getting her entire body painted silver.

Stéphane Sednaoui, director: It was the first time she filmed, I think, in front of a blue screen. We spent the entire day. She can be like, “OK, you know what I’m leaving at 7 and that’s it.” But she didn’t pressure me at all; she was like, “Oh my God, he’s so young and so full of energy.” So, she was very, very sweet with me.

I do like the silver image of her. I think she wanted to do something very “clubbing,” the mix was very “clubbing.” I used to work a lot for The Face magazine and I have this image of being a very “pop culture” artist. And I think they thought, “OK, Stéphane would be perfect to do something that is not the Madonna we know, but another kind of Madonna; more pop, more disco, more club.” So, I think that’s why she went all the way, like, “OK, let’s paint.”

18. “Music” (2000)

Comedian Sacha Baron Cohen was just starting to make a splash as the swagger-filled Brit hip-hop fan Ali G when Madonna tapped him to star as a limo driver in the “Music” video. But when she initally called, he couldn’t believe his ears — in an out-of-character interview with Howard Stern, he recalled how he thought Madonna was actually a very convincing impersonator, and that it took him about 10 minutes to realize just who he was on the phone with. “Madonna loves him,” manager Carissa Howard told the Daily Record at the time of the clip’s release. “He is such a doll. She still can’t stop laughing. She watched the tape and thought he was brilliant — the Peter Sellers of his generation.” The video for the spaced-out “Music” was shot in April 2000, when Madonna was pregnant with her son Rocco. Director Jonas Åkerlund’s resulting product works around that fact thanks to its back-of-the-limo setting and quick cuts — although the clip does nod to its star’s condition at the end, when Madonna flaunts a big necklace reading “Mommy.”

Jonas Åkerlund, director: The treatment had dialogue and stuff like music videos usually didn’t have back then. We wanted to have a comedian and Madonna was really good friends with Chris Rock and some of these other great comedians here. But I had just caught the attention of Sacha Baron Cohen, the Ali G character, out of London. And I talked to her, “Please, you got to check this guy out. He’s awesome” And nobody in America had heard of him. They actually ended up meeting, which was great because that kind of sold it right away.

She was pretty pregnant. I didn’t think it was a problem, like, “That’s cool! Go out and party and being pregnant.” I thought that was awesome. But of course, she wanted to cover it up….That’s why we had that big nice fur on her! She kept that on and then it was a lot of close-ups on her face, you know?

I remember one thing, we had the big discussion on the shoot day: “Fedora or cowboy hat? Fedora or cowboy hat?” Back and forth, back and forth. I think we even shot a couple scenes with a fedora. I think about it every time I go to a Madonna show, up to this day, when I see all the people in the cowboy hats. I think about that moment. “That could have been a fedora, dude!”

When we’re inside the limo, it’s all green screen. The real limo we had, the gold one, the big one? It was so shitty it didn’t have any interior — it was just all fucked up. But the one where she’s with her friends, partying out, we shot that on the stage here in L.A. We actually shot it at the Charlie Chaplin studio which is right across the street from the…strip club. It was very convenient! We just walked across the street to do the strip scene!…I’m kind of known for my strip clubs. [Laughs] I think it was [my idea]. But, I mean, what’s a party night without a strip club? I wouldn’t say that now, but back then, I thought that was [an] important part of the night.

17. “Frozen” (1998)

The frosty video for the first single off Ray Of Light was directed by Chris Cunningham, whose work on the creepy clip for Aphex Twin’s “Come To Daddy” caught Madonna’s attention. “We were thinking of shooting it in Iceland,” Madonna told MTV in 1998. “But then I thought, ‘You know what, I’m going to be freezing. I’m going to be miserable, I’ll be complaining all day, I’ll be sorry that I ever chose a cold place. So I said, ‘Let’s do it in the desert, it’ll be warm.'” The weather, however, didn’t cooperate: “But then we got there and it was like 20 degrees below zero, it was bitterly cold, and I was barefoot. I was barefoot for the entire video, and then it started pouring rain and everyone got really sick, and it just actually turned out to be a really miserable experience.” Cunningham, too, was frustrated by the experience; he originally wanted the clip to be much more elaborate, effects-wise. “The original treatment was, like, massive piles of bodies in the desert. All these figurative sculptures made up of bodies that were all multiple Madonnas,” he said in the book accompanying his Director’s Label DVD. “They were all going to split and break up and change into ravens and then change into dogs. Just a performance video, but a really elaborate one using her, her clothes, and any shapes that would come out of her clothes.” Despite the frustrations, “Frozen” emerged visually stunning: Madonna clad in billowing black, mehndi covering her hands, shape-shifting against a stark desert tableau.

16. “Burning Up” (1983)

Steve Barron was one of the most in-demand music video directors of 1983 after helming Michael Jackson’s “Billie Jean,” Eddy Grant’s “Electric Avenue” and Toto’s “Africa.” Madonna had one single — “Everybody”— to her name, which didn’t chart on the Hot 100, though Warner Bros. knew a superstar when they had one. Barron was going to stay on vacation rather than meet the virtually unknown singer about her latest song, “Burning Up,” a track he says “didn’t speak to me.” “If something came along that was poppier, I wouldn’t even know what to do,” says the director, who recently released, Egg n Chips & Billie Jean, his memoirs of the video age. “It would just be all about pop, and I wasn’t about pop.” Nonetheless, his video stands as a great testament to the anything-goes era of early MTV, juxtaposing disparate images of illuminated busts and cars driving on water with Madonna writhing in the middle of the road. At the end, of course, she takes control of the wheel.

Steve Barron, director: I got a call from [producer] Simon [Fields] in Los Angeles and he said there’s a video to do for a reasonable budget and that this is going to be really big. I was on vacation and didn’t really want to get my head into something at that time. But [Madonna] was really keen on the “Billie Jean” video and I eventually agreed, begrudgingly. I had gotten the track and said I wouldn’t know what to do for that, because it didn’t have the atmosphere that I always look for in a song.

The piece of paper was addressed as the “penthouse suite” so I thought she was rich or had a rich family. When the doors opened [on the top floor of her building], it was crumbled staircases and a paper plate that said “Penthouse Suite” with an arrow pointing up the stairs stuck with tape to a cracked wall. Music was pumping out of that top floor; it was so loud, I yelled out, “Hello!” and yelled again a couple of more times. I pushed a door down the hallway open and there she was, naked except for a pair of knickers, on the floor doing exercises in front of this massive speaker and amp. That was the only furniture in the place really. She seemed very confident with herself.

We shot for two nights in Los Angeles. I basically ended up doing a bunch of ideas from my ideas book as opposed to from the song mainly because I didn’t connect with it too much. It was a bit of a mish-mash of a video. She trusted me, definitely. She handed it over, which she probably shouldn’t have done in retrospect. But she obviously wanted to be very much in control of how she looked and how she was dressed. Her dress was the most important thing that she wanted to talk about.

We were doing shots of her at night lying in a boat as she was singing. We had a seven-ton crane that stretched out over the lake with a camera on it, me and a grip. I was arranging to go right out over the top of her so that we could look straight down on her. The boat was anchored into position and the base of the crane was sitting sloped on this little boat ramp with massive wheels. I was asking, “Let’s get out right over the eyes” and we were about 15 feet above Madonna. I looked back at the ramp and the two back wheels had lifted off by about a foot and a half. No one had noticed. I looked back at it and yelled at the crane operator to stop. The thing teetered; just dropped backwards-and-forth, and he quickly jumped on the switch and started pushing us back, but he didn’t move very fast because you felt if you made any kind of movement, it would have taken that crane down. We were right on the midpoint balance and we would’ve come down on her. She would have been 100 percent dead. It was so close, and I never told her that night because I didn’t want to scare her. We would’ve been in a hospital for six months and she would’ve been dead. Definitely.

15. “Human Nature” (1995)

“When I first called up [Jean-Baptiste] Mondino and I said I wanted to do the video, I said that I wanted it to be more dance-oriented than the things that I had done before,” said Madonna. “Mondino found this book by this illustrator named [Eric] Stanton who does kinda S&M drawings and stuff — but we didn’t want to go for the straight S&M; we wanted to have it be more about making fun of it.” Following a half-decade of sexually charged work — the banned “Justify My Love” video, the explicit Sex book, the thriller Body of Evidence, the entire Erotica album — Madonna and Mondino made a simple statement (“it’s human nature”) with a wink, a smile and some choreography. Dressed in bondage gear, Madonna laughs, makes funny faces and disciplines her Chihuahua with a riding crop in a video that’s kind of like 50 Shades of Busby Berkeley. “The song is about basically saying don’t put me in a box, don’t pin me down, don’t tell me what I can and can’t say. It’s about breaking out of the restraints, ” she said. “So that’s basically the point of the costume.”

Jean-Baptiste Mondino, director: All I know is…my main problem is I don’t like videos when somebody’s dancing, that the camera is moving a lot. I’m more like an old-time, classic guy, because I remember most of the video you had shot with the crane, some Steadicam, plus some panning. So you have about five different cameras shooting a performance, and after they edit like crazy. It gives you a lot of freedom, but I feel very frustrated because I like to see somebody dancing. I hate when there’s too much editing. I like the steadiness of the performance because then you can really enjoy the movement of the body. You see the skill.

I like to shrink — as much as I can — the stage because I can grab her. If not, everyone is running around and I’m not good with this. So I came up with the boxes [laughs] and I knew that with the boxes I had to do with something quite un-expect-able because there’s not too much stage to dance in. So there’s something beautiful about it and they looked like bees or something.

And the rest of it was how to create some kind of choreography and some graphic imagery with the S&M outfits, but with humor. So she has a little dog and she has some funny moments where she drops down, there’s some Charlie Chaplin-esque moments into in it. Because S&M is a game, you know? It’s dark, it looks dark, but I think people have fun. When you wear rubber like this, you better have fun. If not, you stop using it for sex and you become a diver, you know?

14. “Bedtime Story” (1995)

The genesis for this clip came when Madonna approached director Mark Romanek about helming the clip for the Erotica track “Bad Girl.” When they met, Madonna brought a single piece of artwork for inspiration. “It was this very surreal, dark, kind of amber-colored, somewhat disturbing painting — and I didn’t know Madonna, so I was really surprised that this was her taste in art,” Romanek recalled on his Director’s Label DVD. Madonna eventually had frequent collaborator David Fincher direct the “Bad Girl” clip, but when Romanek heard the pulsing, Björk-penned “Bedtime Story,” he knew he had found a video vehicle to show off what he called “painterly surrealism.” Romanek delved into the history of female surrealists, and the end result — which paid particular tribute to painters Carrington and the Remedios Varo — was launched with a splashy pajama party at New York’s Webster Hall in the spring of 1995 and placed in the Museum of Modern Art’s archives. That big launch was commensurate with its budget, thanks to the elaborate visual effects sprinkled throughout. “Bedtime Story” cost a reported $5 million in 1995 dollars, and remains one of the form’s priciest offerings.

13. “Oh Father” (1989)

You have to respect a video that opens with a nod to Citizen Kane and gets more ambitious from there. Working for the second time with director David Fincher, Madonna dug deep for this mini-epic about her mother’s death, her troubled relationship with her father and her tempestuous marriage to Sean Penn. “It’s my most autobiographical work — with a little bit of drama thrown in,” she would tell Cosmopolitan, adding, “It’s boring to be completely autobiographical.” “Oh Father” offers some of the most evocative and disturbing images in all of Madonna’s oeuvre, among them the sight of a young girl stepping up to her mother’s coffin to find that the dead woman’s lips have been sewn shut — which reportedly came from the singer’s memories of her own mother’s funeral.

The song and the video were very personal for Madonna, but, interestingly, it didn’t appear to be her idea to release it as a single. “I had kinda talked Madonna into releasing ‘Oh Father’ as a single and we did this video and we were very happy with the video and nobody ever saw it because the song wasn’t a hit,” Fincher told The Guardian, “so she came back to me and said, ‘You screwed me up. You wanted to make this video for the song and no one liked the song and I went to bat for you and now I have to make a video by Tuesday.’ And I said, ‘What’s the song called?’ And she said, ‘Vogue.'”

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.

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.

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.”

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.

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!'”

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 final cut on the movie, I will remember how she handled that freedom.

6. “Rain” (1993)

Director Mark Romanek’s clips for Lenny Kravitz and En Vogue were high-volume, high-energy affairs that caught the eye of Madonna, who asked him to go behind the camera for this lush Erotica track. “I actually turned her down, because I thought the song was really romantic and I didn’t really know what to do with something romantic at that point in my life,” Romanek said on his Director’s Label DVD. He eventually accepted, and decided to change things up by warping Madonna into the future. “Everything was looking back, and I said, ‘Well, maybe it would be kind of interesting to be something futuristic with Madonna.’ Her knee-jerk to that was, ‘But this song is kind of like Wuthering Heights — it should be black and white, romantic. And I said, ‘Well, that’s a little too kind of on the nose.'” The resulting clip, with Madonna clad in big headphones and being attended to by makeup artists, had a chilly feel, thanks to its high-contrast look and meta-narrative concept. Picking the clip-within-a-clip’s director was a bit of a challenge: “First I think we wanted to have Jean-Luc Godard — and when you’re working with someone like Madonna, that’s a possibility,” Romanek recalled. She reached out to the French New Wave pioneer as well as the Italian director Federico Fellini, but both declined. Japanese composer Ryuichi Sakamoto got the nod, thanks to him being what Romanek called “the most iconic and famous and attractive Japanese icon.”

5. “Like a Prayer” (1989)

“‘Like a Prayer,'” Madonna told the New York Times shortly after this video for the gospel-tinged track came out, “is the song of a passionate young girl so in love with God that it is almost as though He were the male figure in her life.” But thanks to the Mary Lambert-directed clip’s heady imagery, which included burning crosses, stigmata and a saint’s icon not only made flesh but succumbing to its pleasures, “Like a Prayer” wound up becoming about a lot more — the role of religion in popular culture, racism and the way large corporations react when confronted with controversy. (“I think when you fool around with stigmata it’s a fairly dangerous area,” Rolling Stone then-music editor David Wild quipped to Reuters.) The clip caused such a commotion upon its release that Pepsi pulled a $5 million ad campaign featuring the song, albeit with substantially different imagery attached. Still, Madonna remained undaunted: “Art should be controversial, and that’s all there is to it,” Madonna told the Times in 1989, as fundamentalist groups raged and Italian television banned the clip. That philosophy has animated the Material Girl’s work since her earlier days, but the manner in which the “Like a Prayer” clip artfully imbued its ebullient song with her matter-of-fact, yet lightning-rod view of the world around her makes it one of the most iconic videos of MTV’s first decade.

Mary Lambert, director: I knew that we were pushing some big buttons, but I sort of underestimated the influence and bigotry of fundamentalist religion and racism in this country and the world. I always think that, if my work is successful, it goes beyond my intentions and in this case it definitely did. The most important thing was to force people to reimagine their visual references and really root out their prejudices. Using burning crosses to reference racism to religion. Why not a Black Jesus? Why can’t you imagine kissing him? I wanted to speak about ecstasy and to show the relationship between sexual and religious ecstasy. I think that subconsciously a lot of people understood this and were either enthralled or outraged by it. Consciously, I don’t think a lot of the audience would have made this interpretation.

4. “Take a Bow” (1994)

Remembers director Michael Haussman about this love story filmed in Spain, “She said, ‘OK, Here’s the song: It’s about a girl in love with a public figure. Write something, but just don’t make it dark.’ So, of course I went and wrote something really dark.” Madonna and the director met at the Ritz in Paris, tabled the discussion about his dark idea until dinner and started making small talk. “She says, ‘Well, what have you been doing?’ And I said, ‘Well, I’ve been really into filming bullfights and stuff.’ And I just saw this sparkle in her eye and suddenly I just kind of went with it. Pretty sure the while thing was written [that] night.” The sepia tinged video mixes shots of real life bullfighter Emilio Muñoz with Madonna for a clip that’s sensual, majestic and features steamy footage of the pop star writhing in front of a TV. “I thought it was going to be [difficult to direct] but then it was one of the sexiest things that I’ve ever seen,” says Haussman. “She would just play the song through and go for it.”

Michael Haussman, director: It became epic in proportions to try and actually do that video because it was such a taboo subject. There were several times when it was gonna be cancelled because of PETA getting involved, saying, “We understand you’re going to film a bullfight?” And originally I was. I was gonna try to film a bullfight where the bull gets killed and everything, and that was kind of the idea to stay true to it. And [it] became kind of obvious…we can’t stage a bullfight for a Madonna video, that’s not going to go across too well….And sure enough, it was such a fiery topic that we had to have to have the police in my office in London opening our mail because a lot of animal rights groups send letterbombs to scientists and things. The producer had a rose taped to his door and it said, “Hasta la vista, baby!” All kinds of really scary shit. I had to check under hotel under different names, which I’ve never had to do, when I was in Spain.

The bullfighting world didn’t want anything to do with someone that’s gonna come in and [try to be] commercializing them. What helped was that I had a super passion about it…I knew enough that I could say, “Listen: I want Emilio Muñoz and I can tell you about every fight he had last year, every outfit he wore and where he fought.” It was kind of funny because everyone said, “Well, he’ll never do it, Emilio Muñoz — why don’t you look at these other guys that are seeking publicity. And those are the guys you didn’t want! So that was a whole trip in itself — literally sitting in hotels in Seville, waiting to meet this guy. Waiting for four days passing — and it’s only his guys coming to scope you out and see if it’s real and it wasn’t some television show where they do pranks on people.

One thing we had to promise was that we’d never harm the bull in any way. And that became a real touchy subject because a bullfighter can’t really fight a bull unless he’s been harmed in some way. Usually they do a pick to his shoulder and that makes his head go down so that he could go use the smaller, red cloth called a muleta. So, if suddenly, we were not able to pick him or have any trace of blood on the bull, so how is he supposed to use this red cloth? She was set to fly out in two days and he was set to come the following day — it was right down to the wire. So I posed him the problem and he didn’t really say anything except, “OK, let me think about this.” And he just kind of of disappeared for two days. No one could get him on the phone. She gets on an airplane to come out. So, the drama was just fantastic! So he finally arrives and says, to the Spanish press, “I’m going to fight this bull, I’m not going to pick or bandeira him. it’s going to be the first time it’s ever done and I’m going to do it. I’m going to do it for my friend Michael.”

I don’t think [the bullfighting community] ever really wanted it to get out because he was able to fight that bull fine and it was beautiful and the bull never got hurt…at all. But you have to understand the reason that can’t happen is, unfortunately, [bullfighting is] about the celebration about killing of a bull. So it kind of took away the reason it why it exists for the Spanish. And also, when you’re looking at the footage, it’s pretty outstanding what he does. He’s not just fighting it — he’s fighting it beautifully. It’s gorgeous. It was all cloaked in secrecy. He wouldn’t do it unless no one saw. It was just too weird that a bullfighter’s fighting a bull that’s not picked or bandeira‘d

3. “Open Your Heart” (1986)

“At the time, we were into a period where we were experimenting [with] some kind of freedom about the body, about sexuality and stuff. So the peep show was an idea that I had,” says “Open Your Heat” director Jean-Baptiste Mondino. “But there was something sweet about this little boy waiting for her outside — something very naïve and sweet.”

Clad in a black bustier and stripping off her gloves and wig, “Open Your Heart” was Madonna’s first overtly risqué clip. But this was no shock piece: An even mix of Fellini and Fosse, “Open Your Heart” was gorgeous, from the paintings of art deco artist Tamara de Lempicka on the club exterior, to the colorfully cold cast of characters. At one point, in a brilliant piece of synergy, Madonna leans back and mimics the now-iconic Herb Ritts cover photo of “Open Your Heart”‘s album, True Blue. “Because she makes the picture, you know?” says Mondino. “She gives you the stuff. You’ve got to be ready to grab it.”

Jean-Baptiste Mondino, director: [The set was built] from scratch. We found this place where we could actually build it. We just built the front of it and the little booth where the old man was inside. I guess it was my Hollywood period where I was in [a] Hollywood state of mind with my cranes, the building….We were very young [laughs] and everything was possible, I guess. I like the fakeness of it. I haven’t seen it for a long time, but when I saw it once again, I said, “It’s so naïve.” It’s kind of badly done, which I like, compared to today. We didn’t have the same equipment, people are more skillful today, but there’s something sweet about it. I love the ending; like a Charlie Chaplin ending when they run after each other. That little moment is very touching.

The good story about this video is that it was the first one I did with Madonna, and I said to her, “You know it could be nice maybe if you wear a black wig,” because she was kind of blonde. Very well known as being the blonde with short hair. So a few days before the shoot, we had the meeting with hair and makeup and they work on her and they prepare her with the outfit and the wig and stuff. And I came in and they were all raving about, “Oh my God, she’s so beautiful” and stuff. Then she turns around and she looks at me with the wig on and says, “OK, Mondino — tell me what do you think.” And when Madonna asks you something, she asks you something, you know? It’s not just like a sentence; she really meant it.

So I look at her and say, “Well, you look great, but to be honest, I prefer you in blonde.” She looked and me and that day, she trusted me because she knew more than anyone else that she was better in blonde….And I think that day, maybe that’s when I gained her confidence.

2. “Ray of Light” (1998)

“It’s probably, to this day, the longest shoot ever for a music video,” remembers “Ray of Light” director Jonas Åkerlund, who traveled to New York, Los Angeles and Las Vegas to shoot this fast-forward pastiche. “I think we shot 14 shoot days or so. But, we were the smallest crew. My idea was to fit the crew into one car. We found an angle, then we set it up, and then and we were talking shit for a half-hour, waiting for it because it took forever to do these shots.” The clip’s stationary shots with a flurry of activity had a similar feel to 1982 art-house favorite Koyaanisqatsi (which he hadn’t seen) and provided a frantic energy for Madonna’s embrace of contemporary house music. Åkerlund would become the only collaborator in Madonna’s monumental run to garner the pop star an VMA for Video of the Year.

Jonas Åkerlund, director: We did a few tests in Stockholm with a film camera so I could to show her the technique I was talking about, and the test actually came out so good, that it ended up the final video. So there’s a lot of shots from Stockholm in there.

Of course, we didn’t shoot digital — we shot with a big, 35mm camera. We had this diagram that I had in my pocket for the whole production where it said how many frames per minute or per second that we needed to do in order to get the certain amount of footage. So let’s say you shoot one frame every 10 seconds or so? Then you have to do that for 30 minutes to get like five seconds. Stuff like that

We mounted the camera on a bus, I remember, driving around in New York. That was like a pretty big effort for a 20-frame thing [laughs]. Everything was like a huge thing considering how much that actually ended up in the video because it’s happening so fast. Every shot was just like such a big deal. I think we ended up using everything we shot, too. The song was long — I remember in the edit thinking that the song was too long because I used up all the footage.

“At the time, I really didn’t think about [winning the VMAs]. I was there with my Swedish friends, just drinking beer and though it was great that the beer was for free. But looking back, it was a life-changing moment for me.”

1. “Express Yourself” (1989)

The first of Madonna’s collaborations with David Fincher is also her best — and one of the priciest (at $5 million, it was the most expensive video ever made at the time). Heavily influenced by Fritz Lang’s Metropolis, with its sci-fi cityscape and surreal factory scenes featuring men struggling with giant machines, “Express Yourself” is a perfect melding of Fincher’s expressionist impulses with Madonna’s shape-shifting allure. Here, we see her juxtaposed against various versions of herself, each representing a different kind of seduction: A pantsuit-wearing, Marlene Dietrich-like figure with a monocle; a shimmying coquette in a corset; a submissive wife chained naked to a bed. Meanwhile, Fincher’s camera swoops and cranes and tracks around the impressive sets and through fields of blown-out light, expressive shadow, and thick layers of steam. (The director’s feature film debut, Alien 3, would actually repurpose some of this aesthetic.)

“This one I had the most amount of input,” said Madonna. “I oversaw everything — the building of the sets, everyone’s costumes, I had meetings with make-up and hair and the cinematographer, everybody. Casting, finding the right cat — just every aspect. Kind of like making a little movie. We basically sat down and just threw out all every idea we could possibly conceive of and of all the things we wanted. All the imagery we wanted — and I had a few set ideas, for instance the cat and the idea of Metropolis. I definitely wanted to have that influence, that look on all the men — the workers, diligently, methodically working away.”

Both Metropolis and “Express Yourself” end with the same epigraph: “Without the heart, there can be no understanding between the hand and the mind.” But what was for Lang a plea for reconciliation between workers and bosses becomes, for Madonna, a creative credo.