Strike a Pose: Madonna’s 20 Greatest Videos

Taking total control of the artistic process, Madonna worked with director David Fincher to make a sci-fi classic

The first of Madonna's collaborations with acclaimed Fight Club and Social Network director David Fincher is also her most ambitious use of the video form (and, at $5 million, the most expensive video ever made at the time). Heavily influenced by German director Fritz Lang's 1927 classic Metropolis, with its sci-fi cityscape and surreal factory scenes, "Express Yourself" is a perfect melding of Fincher's expressionist impulses and Madonna's shape-shifting allure. ("We sat down and threw out every idea we could," Madonna said.) She played different seductive characters: a pantsuit-wearing, Marlene Dietrich-like figure, a shimmying coquette in a corset, a submissive wife chained half naked to a bed. "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 makeup and hair and the cinematographer, everybody. Casting, finding the right cat – just every aspect. Kind of like making a little movie."

A bold embrace of electronica that got Madonna her due at the VMAs

"It's probably, to this day, the longest shoot ever for a music video," remembers director Jonas Åkerlund, who traveled to New York, Los Angeles and Las Vegas to get "Ray of Light"'s fast-forward cut-and-paste look. The clip had a similar feel to the 1982 art-house favorite Koyaanisqatsi (which Åkerlund had never seen) and a frantic energy that fit the song's embrace of "electronica." 

"We had this diagram that I had in my pocket for the whole production," Åkerlund recalls. "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. Every shot was just, like, such a big deal." The hard work paid off: Although she made nearly 70 music videos during her career, "Ray of Light" is the only one to win an MTV Video Music Award for Video of the Year. Says Åkerlund, "I didn't really think about winning the VMAs. But it was life-changing for me."

Madonna takes a big risk in a risqué video with an art-house soul

"At the time we were into a period where we were experimenting [with] some kind of freedom about the body, about sexuality and stuff," says director Jean-Baptiste Mondino. "So the peep show was an idea that I had." With Madonna playing a stripper clad in a black bustier, "Open Your Heart" was the singer's first overtly risqué clip to date. But it was no mere shock piece: A mix of Federico Fellini and Bob Fosse, "Open Your Heart" featured paintings by art-deco artist Tamara de Lempicka on the club exterior and a colorful cast of cold-looking characters. At one point, in a striking piece of synergy, Madonna leaned back and brilliantly reproduced the now-iconic cover photo for her 1986 album True Blue, which featured "Open Your Heart." "She makes the picture, you know?" says Mondino. "She gives you the stuff. You've got to be ready to grab it."

Madge + bullfighting = one of her weirdest scandals ever

"There were several times when it was gonna be canceled because of PETA getting involved," remembers director Michael Haussman about this steamy love story, filmed in Spain with real-life bullfighter Emilio Muñoz. "The bull never got hurt … at all," says Haussman. "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." Still, animal-rights organizations were furious. "We had to have the police in my office opening our mail looking for letter bombs," says Haussman. "The producer had a rose taped to his door, and it said, 'Hasta la vista, baby!' All kinds of really scary shit."

How to offend every bigot in America in just five fiery minutes

Burning crosses, stigmata, a saint's icon coming to life and succumbing to the pleasures of the flesh – the imagery in "Like a Prayer" caused such a commotion that Pepsi pulled a $5 million ad campaign featuring the song. "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," says director Mary Lambert. "I always think that if my work is successful, it goes beyond my intentions, and in this case it definitely did." Madonna originally wanted to focus more directly on racial violence. But she and Lambert revised and broadened the concept to connect sex and religion, casting actor Leon Robinson as a black saint (presumably Martin de Porres, the patron saint of racially mixed people). "Why not a black Jesus?" says Lambert. "Why can't you imagine kissing him? I wanted to show the relationship between sexual and religious ecstasy." Madonna summed up the clip's mission succinctly, telling The New York Times in 1989, "Art should be controversial, and that's all there is to it."

A trip into the future that Madonna almost didn't take

Director Mark Romanek's clips for Lenny Kravitz and En Vogue were high-
volume, high-energy af
fairs that caught Madon
na's eye, so she asked him 
to go behind the cam
era 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. He eventually accepted and came up with a futuristic concept and the unique idea of staging a video within a video. At first Madonna wasn't sold on the idea. "This song is kind of like Wuthering Heights – it should be black-and-white, romantic," Madonna said to Romanek. But the director's vision prevailed. Madonna reached out to Jean-Luc Godard to appear as her director in the video. When he turned her down, she tried Federico Fellini, who also declined. Finally, they went with experimental composer Ryuichi Sakamoto because he was, according to Romanek, "[an] attractive Japanese icon."

Setting high style aside for a dose of social realism in Staten Island

With "Papa Don't Preach," Madonna began treating music videos more as short films than promotional clips. She imbues 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-bomb image. "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," says director James Foley. The video was shot over three days in Staten Island and Manhattan. Foley recalls that, despite the seriousness of the song, the vibe was "pure fun." "No one was getting down about the social importance of it," he says. "We just liked to blast it as loud as possible."

Creating vintage glamour out of the underground club scene 

Madonna's third collaboration with director David Fincher is a kaleidoscope of classic movie-star iconography and an energetic display of "vogueing," a dance born in the underground gay club scene. Remarkably, the elegant video was prepared in record time for a single that was being rush-released. "We cut this thing together as quickly as we could," recalls Fincher. "We shot the video in, like, 16 hours, that was it. She got on the plane and went on her world tour."

Madonna takes a big-budget trip to Venice and gets down with a lion

"We went to Venice with a bunch of fucking wack jobs," said Warner Bros. creative director Jeff Ayeroff. "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, director Mary Lambert shot the pop star on gondolas in Venetian canals and teamed her with a lion. Lambert recalls, "At one point the lion started sniffing Madonna's crotch, and I thought she might be a goner."

Madge takes the plunge with a first-time director in one of her sweetest videos

The photographer Herb Ritts and Madonna struck up a friendship early in her career. Ritts shot the cover for the 1986 album True Blue as well as Madonna's fourth Rolling Stone cover, in 1987. But what Madonna really wanted Ritts to do was direct music videos. "She kept asking me, and I said I really didn't know the first thing about moving imagery," Ritts said 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 the camera work as well. It was invigorating." In the video, Madonna playfully frolics in black-and-white on the beach, and even dives into what was actually freezing water. Said Ritts, "She was a real trouper."

A tribute to Marilyn Monroe that became a classic itself

"I have always been extremely interested in Marilyn Monroe – her life and persona. Madonna and I shared that fascination," says director Mary Lambert. "I watched the dance sequence from Gentlemen Prefer Blondes about a million times with [choreographer] Kenny Ortega, who brilliantly reinterpreted it [in the video]." By now, this homage to Marilyn Monroe's 1953 film has probably inspired as many tributes as the original: Taylor Swift's performance of "Shake It Off" at the 2014 MTV Video Music Awards was definitely more Madge than Norma Jean. Says Lambert of Swift, "I think she's amazing, and I was flattered."

A hotel party that made for the steamiest video of her career

MTV refused to play this Jean-Baptiste Mondino-directed clip, which featured images of S&M, group sex and even some bare breasts – but the resourceful Madonna spun the controversy into the bestselling "video single" of all time. "The whole idea was to lock ourselves into this hotel for three days and two nights, without any rules," says Mondino. "Nobody was allowed to go out. It was very strange because we didn't know when we were doing the film or when it was real, you know? Things were just happening. The last morning when I woke up and had to go back home, I felt very strange on the sidewalk."

Childhood memories haunt a deeply personal mini-epic

Madonna dug deep for this David Fincher-directed, Citizen Kane-referencing 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," she said. In one disturbing scene, a young girl steps up to view her mother's coffin only to find the dead woman's lips have been sewn shut – an image reportedly inspired by Madonna's memories of her own mother's funeral.

Madonna fans get a crash course in "painterly surrealism"

The idea for this clip came when Madonna approached director Mark Romanek about doing the video for the 1992 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. When he later heard the pulsing, Björk-penned "Bedtime Story" a couple of years later, he knew he had found a vehicle to show off what he called "painterly surrealism." Romanek delved into the history of female surrealists, paying particular tribute to painters Leonora Carrington and Remedios Varo with elaborate visual effects. The end result cost a reported $5 million, making it her priciest clip since "Express Yourself."

Laughing her way through a playful S&M fantasy that co-starred a dog

After a decade of sexually charged work, Madonna and Jean-Baptiste Mondino addressed erotic subject matter with winking humor. Dressed in bondage gear, Madonna laughs, makes funny faces and disciplines her Chihuahua with a riding crop. "S&M is a game," says Mondino. "It's dark, it looks dark, but I think people have fun."

The early-Eighties clip that almost cut Madonna's career short

This testament to the anything-goes era of early MTV was the work of Steve Barron, who was in high demand at the time after his success helming videos like Michael Jackson's "Billie Jean" and Eddy Grant's "Electric Avenue." Barron didn't love "Burning Up," but he took the job. Of their first meeting, held at Madonna's apartment, he recalls, "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." Barron came up with a "mishmash" of ideas and shot over two nights in L.A. At one point, a massive crane on the set started teetering and nearly fell on Madonna. "She would have been 100-percent dead," says Barron. "I never told her that night because I didn't want to scare her."

Chilling out on a desert vacation in a trippy experimental clip

This arty video was directed by Chris Cunningham, whose work on Aphex Twin's creepy "Come to Daddy" caught Madonna's attention. "Frozen" was visually stunning, with Madonna clad in billowing black against a stark desert tableau. But it wasn't easy to make: "We were thinking of shooting it in Iceland," she said in 1998. "But then I thought, 'You know what, I'm going to be freezing. I'm going to be miserable.' … So I said, 'Let's do it in the desert, it'll be warm.' … But then we got there and it was like 20 degrees below zero … and I was barefoot."

A pregnant Madonna and a little-known Sacha Baron Cohen take a wild ride

The girls-night-out-themed "Music" video was shot in April 2000, when Madonna was pregnant with son Rocco. "I didn't think it was a problem," says director Jonas Åkerlund. Madonna didn't agree, and spent most of the video in a fur coat. "Music" was many Americans' introduction to comedian Sacha Baron Cohen, who played a limo driver. "I remember one thing," says Åkerlund. "We had a big discussion: 'Fedora or cowboy hat?' Every time I go to a Madonna show and see all the people in cowboy hats, I think 'That could have been a fedora, dude!'"

Madge gets her martyr on and receives a paint job

"My concept was that she was a kind of Joan of Arc," says director Stéphane Sednaoui. "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 was worried I'd burn her." While Madonna doesn't catch fire in the clip, she does get evocatively covered in silver body paint: "They thought, '[Let's] do something that's not the Madonna we know – more pop, more disco, more club,'" recalls Sednaoui. "So, I think that's why she went all the way, like, 'OK, let's paint.'"

How to power through pain in the name of a good dance sequence

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 several broken bones. But she still managed to don a long-sleeved pink leotard and danced around a rehearsal studio with gusto. "She was such a trouper. She just fell off a horse!" said director Johan Renck, who assembled her segments from a three-hour shoot, taking breaks so Madonna could deal with intense physical pain. Renck, a last-minute replacement for David LaChapelle, didn't have time to overthink its dancing-in-the-streets concept: "I like being out on a limb and not know what we're doing and why. Just deal with the mayhem, you know?