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The 13 Greatest Madonna Music Videos Of All Time

The 13 Greatest Madonna Music Videos Of All Time

Madonna is, to put it simply, the greatest music video artist of all time. Sure, Michael Jackson has the best video of all time with Thriller, but in terms of sheer amount of classic music videos, Madge has him, any just about every other artist, beat. At 67 videos over thirty years (and counting) no other pop star embraced the concept of the music video like Madonna has. And at 56 years old, she shows no sign of slowing down, having just released her latest video Living for Love this week on Snapchat, just prior to her performance at the Grammy Awards this Sunday.

But among that many videos, which are the cream of the crop, the best of the best? I should point out, this is NOT a “Madonna’s Greatest Songs” list–many of her best songs don’t have videos that are that great, especially songs from movies soundtracks like Into The Groove, Crazy For You, Live To Tell, I’ll Remember and others, which had videos that were just clips from the movies they were in edited together, which automatically disqualifies them to me. And Holiday, one of her most iconic songs, never even had a proper video, believe it or not. As to why  a top 13 videos, and not top 10 or top 20, well…the number 13 is actually a lucky number in the Kabbalah, so I figured it’s a number Madonna herself would approve of.

13. Burning Up (1983)

It was difficult to decide which music video from Madonna’s original “Boy Toy” era to include in this list; arguably videos for Borderline, Lucky Star and Like A Virgin were all associated with bigger hits than this song, but there is something about Burning Up that is just so ’80s, and so Madonna–the rubber bracelets, the chains, the bleach blonde hair with the terrible roots. When girls today dress up like “80’s Madonna” for Halloween, it’s the look from this video they’re emulating. (Also, the video has a laser beam go though a pair of sunglasses-that’s as ’80s as it gets.)

Burning Up was actually the first real video shot for Madonna’s debut album, but the single died quickly on the charts upon release in 1983, never cracking the Billboard top 100. When Madonna finally hit it big with Borderline and Lucky Star, MTV was desperate for other Madonna videos to air, so they dug up Burning Up from the circular file and started playing it on heavy rotation, which makes people think it was a big hit single, but it never really was. Nevertheless, this iconic video is a classic now, and because of it Burning Up is considered one of her greatest hits, even though it really wasn’t.

12. Deeper and Deeper (1992)

The second single off of Madonna’s controversial Erotica album, this dance song is a tribute to ’70s era disco, and all the wild hedonism, and extreme fashion, that went with it. (the ’90s were just as obsessed with the ’70’s as we are now with the ’90s; it’s the eternal 20 year pop culture cycle.) The song itself is told from the perspective of a young gay boy discovering himself in the club scene.

In the video, Madonna channels Andy Warhol starlet Edie Sedgwick heading out for a night on the town, and even former Andy Warhol star Udo Kier himself makes an appearance. Also making cameos, Madonna’s BFF, actress Debi Mazar, future film director Sofia Coppola, and porn producer/drag queen Chi Chi LaRue. Although a mostly low budget affair, this video perfectly captures the euphoric joy of just losing yourself in the beat on the dance floor.

11. Hung Up (2005)

Hung Up was the lead single off of 2005’s Confessions on a Dance Floor album, arguably the last truly great album of Madonna’s career. Coming off her her 2003 American Life record, her first honest-to-goodness flop, Madonna had a lot to prove. With more than 20 years in the business at the time, did she still have it?

As it turned out, Hung Up went to #1 in 41 countries, and was top ten hit in the US, so that answered that question. Sampling ABBA’s  Gimme Gimme Gimme (A Man After Midnight) this video was another ode to Madonna’s ’70s disco youth, with Madonna rocking the Farrah hair and proving that at 46, she could still work a pink leotard like nobody’s business. The video also showcased Madonna’s incredible talent for finding the best young dancers in the world and snatching them before anyone else does (and, occasionally dating them too.)

10. Frozen (1998)

Frozen was Madonna’s first video and single from her Ray of Light album, which was a massive critical and commercial comeback for her when it was released in 1998. Ray of Light was her most personal album to date, and her mix of pop with electronic music showcased just how much she had really matured as an artist since the “boy toy” days. This video, directed by Chris Cunnigham, envisions Madonna as a kind of gothic witch, floating above a desert landscape, and morphing into various animals (all black of course.) It was striking and evocative and ethereal, and showcased Madonna as we’d never seen here before.

9. What It Feels Like For a Girl (2001)

Directed by Madonna’s then-husband Guy Ritchie, to quote Kill Bill, this video was “a rip roaring rampage of revenge” as Madonna takes out every girl’s frustration about living in a misogynist society on every man in her path. Guy Ritchie’s stamp is all over this video, with his penchant for comedic violence, and therefore this is also one of Madonna’s funniest videos to date. The version of the song used in the video, from her 2000 album Music, is actually a remix, and not the version found on the album, only the second time that Madonna has ever done that. The first time? The video for Express Yourself.

8. Bedtime Story (1995)

By 1994, Madonna had cooled off as the world’s biggest female pop star, overshadowed by the likes of Mariah Carey and Celine Dion. Her first single Secret, from her album Bedtime Stories, did ok, but it was the second single, the ballad Take A Bow, that was an unexpectedly huge hit, spending 7 weeks at #1.

Using the clout from the success of Take A Bow, Madonna convinced her label Warner Brothers to produce what was the then one of the most expensive videos of all time, the Bjork written, electronica twinged Bedtime Story. Directed by Mark Romanek, this surreal tour de force got decent airplay, but the single was too weird for pop radio and never charted. Nevertheless, this remains one of Madonna’s most visually stunning music videos ever, and was a precursor to much of what we’d see from Madonna in the next few years.

7. Nothing Really Matters (1999)

Madonna’s fourth and last single from her Ray of Light album, it didn’t meet with nearly the same success as the previous singles did. Nevertheless, it’s maybe the most interesting video from the Ray of Light era. Inspired by the book Memoirs of a Geisha, Madonna, wearing a series of kimonos created by frequent collaborator Jean-Paul Gaultier, dances around while being intercut with various shots of people of Japanese descent, who are moving around in a creepy, almost robotic way. It’s a weird, off putting visual to place with such an uplifting song, but then maybe that contrast is why it’s so interesting. By wearing the costume of a geisha, Madonna crossed off yet another female archetype to embody off of the list. (next would be the “cowgirl” phase.)

6. Open Your Heart (1986)

In the third video from Madonna’s massively successful True Blue album, Madge plays an exotic dancer in perhaps the weirdest and most awkward peep show of all time. Dressed like a mix of Marlene Dietrich and Liza Minelli in Cabaret (one of many times she’d pay homage to film stars of the past) she dances for the patrons in the club, while being stalked outside by an obsessed little boy (who is supposed to be her son maybe?) who wants her to leave the show and come with him.

At the end of the video, she decides to leave the creepy patrons at the peep show behind and run off with the little boy and dance the day away in a more wholesome manner, and with a lot more clothes on. This is the video that introduced us to the infamous cone bra that Madonna would put through several permutations over the next several years, and was also the first time she’d work with director Jean-Baptiste Mondino, who would direct another five videos for Madonna over the next twenty years, including our #5 entry on this list….

5. Justify My Love (1990)

1990 was, in many ways, Madonna’s best year of her entire career; she started off the year with one of her most successful hits ever, Vogue, then embarked on her iconic Blonde Ambition world tour, starred in a movie that didn’t bomb for a change (Dick Tracy) and finished off the year with her first greatest hits compilation, The Immaculate Collection, which remains the second biggest selling album from a female recording artist. The first of two new songs on the collection was Justify My Love, a song co-written with a young Lenny Kravitz.

Justify was an ode to sexual desire, and had a video that was deemed too racy for MTV at the time, with Madonna making out with a woman, implied group sex, and cross dressing. So what did Madonna do? She ended up selling it as a VHS single, and it became the biggest selling music video single of all time, and the song itself went to #1. Justify My Love ended up being phase one in what would be Madonna’s “Sex Book” phase, where most of her work had the tinge of vintage black and white porn reels combined with artsy/fartsy student films, but it never worked better, or was sexier, than with Justify My Love.

4. Oh, Father (1989)

This is the video Madonna didn’t want to get made, but that ultimately led to her greatest video of all time. Oh, Father is an autobiographical song from her Like A Prayer album, but Madonna knew it was probably too depressing and down beat to release as a single. Nevertheless, director David Fincher (you might have heard of him) insisted that this was the next video he wanted to make from her album. Real money was spent, and although the video got MTV airplay, the song itself never cracked the top ten, a first for Madonna in six years.

Regardless, the video is a beautiful and sad look back for Madonna at the death of her mother and her rocky relationship with her strict father (although her father was not an alcoholic or physically abusive in real life–that part was allegedly meant to represent someone else, her recently ex-hubbie Sean Penn.) Since the single for Oh, Father never charted, Madonna said that Fincher “owed her one”, and got him to direct her next video (see entry #1)

3.  Like A Prayer (1989)

Madonna’s lead single from the album of the same name, Like A Prayer remains her most controversial video of all time. directed by Mary Lambert, who directed the videos for Borderline, Like A Virgin and Material Girl, this video was actually a morality tale of a white woman who sees a violent crime against another woman, and then sees the police arrest the wrong man for the crime simply because he’s black. She goes into a church to find solace, and that’s where the controversy kicks in. A statue of a black saint comes to life (and not “black Jesus”, as often described by those who never went to Catholic school) and kisses her in a church, clearly turning Madonna on. Add to that the dancing in front of burning crosses, and conservative America went and lost its collective mind.

Pepsi Cola had just paid Madonna a cool $5 million to be their spokesperson, and they had just shot a commercial with her featuring the song, but only aired it once, as almost right away many of the bottling companies in the South threatened to boycott over the racially and religiously charged video, not to mention the Pope, who urged people to boycott Madonna as well. Pepsi quickly pulled their Madonna sponsorship (although Madge kept the $5 mil.) 25 years later however, the controversy is just a footnote, and what remains is a great song with a powerful video that remains one of Madonna’s very best.

2. Express Yourself (1989)

Madonna’s first collaboration with director David Fincher, this ode to the 1927 silent film classic Metropolis was groundbreaking in many ways; it was the most expensive video ever made at the time, costing $5 million dollars, with every dollar showing on the massive Art Deco sets. Madonna used Express Yourself to thumb her nose at sexist music video conventions of the day, most of which had scantily clad women hanging around as sex objects for male rocks stars. Instead, Madonna littered the set with hot muscular men and made them the sex objects (Madge already had a huge gay following, but the Express Yourself video just cemented it for all time.)

In the video she plays both the “male” role overseeing the workers, as well as the glamorous femme fatale, slinking across the room and stroking her black cat. Madonna had more input into the making of this video than any other; in her own words “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.” The song itself was an anthem for female empowerment, and when asked in an interview what the theme of the video and the cat metaphor represented, she simply said “that pussy rules the world.”

#1. Vogue (1990)

Could #1 on this list have been anything else? Vogue is not only Madonna’s most iconic video ever, it’s one of the most iconic videos from any artist, period. In 1999, Rolling Stone voted it the second best music video of all time, only behind Michael Jackson’s Thriller. Originally slated to be the B-side of another single from Like A Prayer, Madonna and her producers came up with the song after the album was already out, but quickly realized it was too good to waste as anything but a single on its own.

Shot in just two days, the video for Vogue is an example of all the right elements coming together at just the right time: Madonna took the vogue dance craze that was so popular in the gay/drag ballroom scene of late ’80s New York (captured so well in documentary Paris Is Burning) and then combined it with an immaculately staged homage to the golden age of Hollywood glamour, and got one of the best directors of the time, David Fincher, to direct, and voilà -instant classic. Of course, as with most things Madonna, this one was no stranger to controversy either, as Madonna’s breasts were fully visable under the sheer blouse she wore in parts of the video. MTV threatened to not air it, but Her Madgesty threw her weight around, and got her way. In the end, I’m sure MTV was happy she did.


Did I forget a classic Madonna video, and you want to tell me which one I was a total dummy for leaving off? (if you say Material Girl or Erotica, I might even be inclined to agree with you.) Let us know in the comments below.

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  1. daniel says:

    Borderline!  Lucky Star!  Like A Virgin!  

  2. Carlos says:

    Bad Girl (1993) directed by Davis Fincher