Back in 2015, I revisited all of Madonna’s videos to celebrate seeing her in concert for the first time. Unfortunately, time slipped away from me and I didn’t get a chance to finish ranking her videos. Okay, so maybe I just forgot. Either way, it’s time to pick up where we left off. The 90s were a challenging time for Madonna. It’s the period that saw her push the boundaries of sex, which caused a huge backlash. As a result, the era features some of her most controversial and some of her most tame videos. So let’s take a look back at Madonna’s most risque period and rank these clips from best to worst.
Madonna has had a number of memorable videos during her career, but this is the definitive one. This beautifully shot back and white clip is dedicated both to old Hollywood and the underground voguing scene. Madonna looks glamorous as she lists the biggest actors of yesteryear, like Bette Davis, Rita Hayworth, and Fred Astaire. Meanwhile, backup dancers pull do their best voguing while looking dapper in fresh suits. The entire video does a great job of recreating the look and vibe of 1930s Hollywood. And it’s timeless. It’s always been one of my favorites just for how gorgeous she looks. This has got to be one of her greatest videos both for its look and just because the song is so damn good.
“Justify My Love” (1990)
When this premiered, Madonna was no stranger to controversy as she previously stirred up trouble with “Like a Prayer,” but this video pushed boundaries to a whole different level. This was also the start of her oversexualized, Sex era. It’s all about exploring, being free, and enjoying your sexuality even if goes against the norm. Images of BDSM, orgies, male on male, girl on girl, doms and divas run abound as Madonna seduces and gyrates against her leather clad lover. Featuring many androgynous and ambiguous people, the video was ahead of its time showing everything isn’t as black and white as society wants to believe. The clip ends with an energized Madonna leaving the hotel room laughing and fulfilled. MTV swiftly banned the video, which prompted the singer to release it as a VHS single. It has since gone down in history as one of the most scandalous and steamy videos. But little did the world know that Madonna wasn’t finished exploring her sexual realms.
“Take a Bow” (1994)
This beautifully shot video sees Madonna yearning for her lover, real-life bullfighter Emilio Munoz. The entire video is a parallel between Madonna and Munoz’s abusive affair and his bullfight. We see both of them getting ready, making a grand entrance, and the bloodshed both from the bull and Madonna herself. Other shots include Madonna in sexy underwear while she gets a little too friendly with her television, which is broadcasting Munoz’s image. Because of the vintage style and the way it was shot, it’s one of her most memorable videos.
“Human Nature” (1995)
Madonna took quite a beating for her over-sexualized image. This video and song was her response to her critics who thought she went too far. The singer gives her haters a big fuck you while she struts around in a catsuit. The video is filled with bondage and S&M images, such as the singer tied to a chair, her wearing what looks like a gimp mask, and her brandishing a whip, which she then uses playfully on a dog. All of this is supposed to represent breaking out of restraints and not having any shame. This has always been one of my favorites because of how fierce she is. She’s a complete badass who’s tired of trying to please her harshest critics. This is the strong, badass diva I originally fell in love with. Her tame videos showed she knew how to be modest and vulnerable, but here she took back her dominating image, which is when she’s at her best.
“Bedtime Story” (1995)
This is Madonna’s weirdest video. It’s even a bit disturbing. It’s filled with many bizarre images that probably have some symbolic meaning, like Madonna giving birth to a flock of doves or the creepy-ass scene where her lips replace her eyes. All these scenarios are supposed to represent various surreal dreams which borrow elements from new age, Sufi, and Egyptian cultures. I always thought the video was unnerving, but it also intrigues me because it’s so different. Many of Madonna’s videos are simple and play up her sexuality, but this one is full of freaky visuals to shock viewers and get them thinking. Even if you don’t get all the imagery, you’ll get hypnotized by the trippy video. Also, is it any surprise that this was directed by Mark Romanek, the director of “Closer?”
Shot in black and white, this video features Madonna singing in a club, while shots of people in Harlem are mixed in. Throughout are images of drag queens, transvestites, prostitutes and pimps, rebirth, and damnation. Madonna returns to her penchant for playing with religious imagery in a scene where what looks like holy water is dripped onto her forehead. The video ends with her going to her lover’s house where he’s playing with his son, the supposed secret. It’s simple, yet effective. It’s another beautifully shot video with Madonna remaining sexy yet classy. It does a great job spotlighting Harlem and various people who often feel marginalized.
“You’ll See” (1995)
Not only is this an underrated ballad, the video is pretty cool. Serving as a follow up to “Take a Bow,” Madonna and Emilio Munoz reprise their roles as lovers, but this time things are different. Rather than Madonna chasing after him, it’s Munoz that chases Madonna all across the world. In the end, she frees herself from him. There are some gorgeous shots of Madonna singing about being able to make it by herself after all. Another version of the video was shot for the Spanish version of the song “Veras,” which was released only in Latin America. This version features the same scenes from the original interspersed with scenes of Madonna singing in Spanish.
“Deeper and Deeper” (1992)
This 70s inspired video pays tribute to both Andy Warhol and Italian director Luchino Visconti. Madonna’s character is inspired by model and Warhol protégé Edie Sedgwick. Most of the video takes place in a club where Madonna walks around with balloons mixed with shots of her hanging out with her girlfriends, watching a male stripper, and looking pretty bored. But there’s also a weird subplot where Madonna gets entranced and tries to escape a diabolical man. It’s a decent video with several references to the 1970s and Warhol, including a scene where the girls eat bananas, a possible reference to Warhol’s album cover for the Velvet Underground. You may not get all the references and symbolism at first, but at least it’s a fun video.
“I Want You” (1995)
Madonna plays the rejected, vulnerable lover in this clip. Wandering around her apartment in a nightgown, she sits by the phone waiting for someone to call. She goes from anxious worry to fury as she plots the best way to win back her lover. She spends most of the video lying in bed distressed, waiting for the phone to ring. Finally, the phone rings, but as she goes to pick it up, she has a moment of clarity and hangs up. It’s not an exciting video, but it fits the style of the ballad. It also encourages a woman’s strength and independence. It may have been torture, but in the end, she figured she shouldn’t chase after someone who doesn’t want her.
People who thought Madonna went too far with “Justify My Love” clearly weren’t ready for “Erotica.” The video is an onslaught of footage from her Sex photo shoot mixed with the singer miming the track while dressed as a dominatrix. Madonna tries to shock us with images of nudity, S&M, and bondage, but at this point, the media grew tired of her antics. A Madonna backlash began both from critics and fans who felt she went too far. Ultimately, you can view the video as one long advertisement for her baffling Sex book, which featured the singer in various comprising positions. Despite her efforts, the video isn’t as enticing or sexy as her previous ones. It’s just uncomfortable and awkward to watch. She’s trying too hard to be shocking. No surprise that MTV banned this video after airing it only three times after hours.
“Bad Girl” (1993)
This is a classic live fast, die young, and leave a beautiful corpse tale. Madonna plays a woman who lives a life of drinking, smoking, and promiscuous sex. As she walks down this dangerous road her guardian angel, played by Christopher Walken, watches over her. But no matter how hard he tries, he can’t save her. She ends up dying at the hands of a lover. The video tries to have this dark tone with the lesson of being careful what you do, but it’s hard to take seriously. The message is heavy-handed. And I can’t get over the scene of Walken dancing – it ruins the tone of the video. At least the video tries to do something different and stands out from her usual clips. But compared to the classics, it’s pretty forgettable.
With the Powerpoint graphics, various costumes, and lots of dancing this video seems like it was made solely for nightclubs. It’s four minutes of Madonna in different costumes, including a Balinese Idol, and body paint, intense close ups, and lots of gyrating hips. But the actual star of the video is the gold painted muscle man. His overly chiseled body and his aggressive dancing is almost disturbing. On top of that, some of the visuals are so blinding and annoying they’ll give you a headache. After the first minute, I was bored with the video. It seems like something you would put on during a party just to get people on the dance floor.
“This Used to be My Playground” (1992)
Prior to this, Madonna released one of her most controversial videos to date. So how does she follow it up? With a tame, somewhat dull performance video. Most of it is footage of her singing in different photographs while someone flips the photo album pages. This is mixed with footage of the film A League of Their Own, which Madonna was in. It’s not a terrible video but watching someone turn pages for four minutes isn’t very exciting. Rumor has it that the singer stole the idea from Boy George, who used the concept for his 1987 single “To Be Reborn.” At least the movie scenes don’t make up the entire music video. Considering the backlash that followed Sex, it’s understandable why she’d want to tone things down. But I feel this is when Madonna is at her dullest. It’s nice to see a different side to her, but it leads to some forgettable videos.
This is one of those highly stylized “futuristic” videos that became popular in the 90s. With odd furniture pieces all painted chrome, this is a video within a video as we see Madonna filming the clip for the song mixed with footage of her writing and practicing her moves. The singer looks almost unrecognizable in a cropped black wig, which may be an homage to Liza Minelli. What is interesting about the video is it was filmed entirely in black and white then hand painted with blue tones. Seems like a lot of work for a mediocre clip, but somehow it won two Moonmen at the 1993 MTV Video Music Awards.
“I’ll Remember” (1994)
This is another “behind the scenes” video where Madonna records the song in some weird studio while clips from the movie With Honors plays behind her. Meanwhile, she’s directed by producers lurking in the shadows. Eventually, it’s revealed that one of these hidden people is actually Madonna in androgynous gear. Since it was made after her backlash, it’s another tame, boring video. Almost nothing happens. She’s back in the black wig, singing, and holding her headphones, which all musicians seem to do in the studio. A forgettable video for a forgettable movie.
Madonna’s videos don’t end here. Make sure to come back for the fourth part in the Madonna Rank the Videos series. And let me know which one of these videos is your favorite in the comments!