The Iconic Showdown: MJ vs. Madonna


Starry, Starry Night

True icons do not come along too often. Jesus was an icon. Paris Hilton wishes she were. When it comes to popular music, I would say that only five artists really make the list no questions asked: Elvis (natch), The Beatles, Bruce Springsteen, Michael Jackson, and Madonna. Cases could be made for Aretha, Joni, the Rolling Stones, Prince, and Mariah, but I don’t know; they’ve all got serious creds, but there’s still wiggle room for doubt, while the first group are unquestionably in like Flynn.

Of that exclusive group, MJ and Madonna stand out; they really were the most famous, the most infamous, the most talked-about, the most publicity-obsessed, the most video-savvy, the most bizarre, the most interesting, the starriest stars pop music has ever seen. At the Video Music Awards, Madonna talked about the things she had in common with the late Michael, bringing up their Midwestern upbringings and their large number of siblings. There’s actually something else of interest that they share: they’ve both had twelve #1 hits on the Billboard charts. So it’s without further adieu that I present you the Battle of Number Ones between these two timeless legends. Twelve rounds to the finish: who will reign supreme? Let’s find out.

ROUND ONE: Ben (1972) vs. Like a Virgin (1984)

Michael’s career of course started with his brothers, and the Jackson 5 actually hit #1 with their first three singles. Michael sporadically recorded solo records on the side, and “Ben” became his first #1 when he was just 13 or 14 years old. On the other hand, Madonna was a full decade older when she scored her first #1 hit with “Like a Virgin.” It really was the record that unleashed the Madonna phenomenon onto the world, much of it thanks to her writhing-on-the-floor rendition at the VMAs. Interestingly, some people have noted the similarities between the beats of “Virgin” and MJ’s earlier smash, “Billie Jean.” Madonna herself emphasized the connection by throwing in a couple of lines from “Billie Jean” when she performed the song during the Virgin Tour.

Winner: Madonna. “Ben” is sweet, but it’s on the edge of being syrupy. “Like a Virgin,” in contrast, was a lioness declaring herself to the world.

ROUND TWO: Don’t Stop Til You Get Enough (1979) vs. Crazy For You (1985)

It was seven years after “Ben” that MJ really came into his own. His Off the Wall album established himself as not only a solo artist but as a man, not a boy. “Don’t Stop” is a disco classic showcasing MJ’s falsetto. For Madonna, “Crazy For You” was just the continuation of Madonnamania, while also surprising many who didn’t think she had the vocals to pull off a slow ballad.

Winner: It’s a close one, but Madonna takes it again. There’s a reason why the disco craze didn’t last. It just doesn’t age well, especially compared to a sexy ballad.

ROUND THREE: Rock With You (1979) vs. Live To Tell (1986)

This is by far the toughest round yet. Both songs are truly amazing. MJ finds a midtempo groove on “Rock With You” and rides it into pop heaven, while Madonna had to reach deeper than she ever had for her darkest song yet.

Winner: Madonna by a hair. “Live To Tell” is arguably the most emotionally affecting song in Madonna’s canon, with probably the best lyrics she’s ever written.

ROUND FOUR: Billie Jean (1983) vs. Papa Don’t Preach (1986)

“Billie Jean” marks the point when Michael undeniably became the King of Pop. He broke down every barrier there was, simply by making music that was too damn good to resist. Meanwhile, Madonna was busy creating a political firestorm over her teen pregnancy saga.

Winner: Michael. I like “Papa” just fine, but it doesn’t hold a candle to “Bille Jean.” Even now, the thumping bass kicks in, and the song has you in the palm of its hand.

ROUND FIVE: Beat It (1983) vs. Open Your Heart (1987)

Michael’s grip on the world continued with the anti-violence “Beat It” while Madonna was courting controversy yet again, this time by playing a stripper (I think) and kissing (innocently, I think) a boy on the lips in the video for “Open Your Heart.”

Winner: Two in a row for Michael. I actually find “Open” to be one of the most annoying Madonna singles ever. It’s a bit too repetive, and her vocals come off too bratty (not sexy-bratty, which would be good, but just bratty).

ROUND SIX: I Just Can’t Stop Loving You (1987) vs. Who’s That Girl? (1987)

Hey, we’re actually at the same time for both MJ and Madonna! (I was feeling like the guy in the Time Traveler’s Wife for a while) In 1987, we found MJ making sweet love to Siedah Garrett (who would later be Madonna’s back-up singer on tour!) and Madonna singing in Spanglish for the sake of a box office disaster of a film.

Winner: Michael again. “I Just Can’t” is a simple love song, but his vocals are creamy and dreamy, while “Who’s That Girl” is so forgettable that it was actually later left off of her Immaculate Collection CD. (It’s gotta be the first time in history that a #1 hit was left off of a greatest-hits album.)

ROUND SEVEN: Bad (1987) vs. Like a Prayer (1989)

With “Bad,” MJ returned to fighting gang violence with the power of group choreography, while Madonna was busy pissing off the Vatican in “Like a Prayer.”

Winner: Madonna in a no-brainer. “Like a Prayer” was Madonna at her very best, controversial but clear-eyed, sexy but with substance. Meanwhile, “Bad” was so over-the-top both as a song and a video that it came off like a Michael Jackson parody instead of the real thing.


MJ--Trying Not To Look

ROUND EIGHT: The Way You Make Me Feel (1988) vs. Vogue (1990)

Michael returned to form here with perhaps his sexiest vocals ever. Madonna used an underground dance form to make herself into even more of an icon than she already was.

Winner: Madonna. Two awesome songs here, but how could anyone refuse M’s command to “strike a pose”? Just. Not. Possible. Plus, that whole “Greta Garbo and Monroe” rap is the best Madonna bridge EVER.

ROUND NINE: Man In the Mirror (1988) vs. Justify My Love (1990)

The message of “Man In the Mirror”: Don’t judge others. The message of “Justify My Love”: Don’t f*ck others, just me (and tell me all about how you’re gonna do it).

Winner: Michael. “Man In the Mirror” is one of his best songs, finding him clear-eyed and right on the point. Meanwhile, Madonna begins her sex-crazed downward spiral that will find her publishing a book where she’s sucking on toes, shaving off her eyebrows who-knows-why, humping Willem Dafoe on screen (I don’t really get why scrawny, slightly creepy Willem keeps getting called to do sexually explicit movies), swearing approximately 1,447 times on Letterman, and dating both Vanilla Ice and Dennis Rodman.

ROUND TEN: Dirty Diana (1988) vs. This Used To Be My Playground (1992)

Michael decides to rock out (a la “Beat It”) and scores his fifth(!) #1 from the Bad album. Meanwhile, Madonna releases a sad, delicate ballad from the League of Her Own Soundtrack right before she goes on her rampage and the public and the media both decide they’re sick of her.

Winner: It’s a close call, but I’ll go with Michael on this one. Neither song is all that great, but at least “Dirty Diana” has some life to it. “Playground” seems almost anemic in comparison.

ROUND ELEVEN: Black Or White (1991) vs. Take a Bow (1994)

Michael proves that a call for racial equality can be catchy as all heck (though the original video with the whole crotch rubbing and car smashing was one of Michael’s most baffling moments, which is definitely saying something). Madonna, no doubt sick of getting beat up in the press, tones down the raunch and instead goes for elegant tenderness with “Take a Bow.”

Winner: Yet another epic battle. Dangerous was really the last album when Michael still seemed capable of enjoying his music and his life. “Black Or White,” as political as its message may have been, was marked more by pure joy than anything else. Still, I can’t help thinking that it’s slightly edged out by “Take a Bow,” which is an absolute classic. Madonna’s vocals are perfect in the song, both sad and lush, and the melody is as pretty as they come. “Take a Bow” ended up being Madonna’s most successful single ever and almost single-handedly rescued her career (the artsy video also reportedly convinced Alan Pakula to cast her for “Evita”).

ROUND TWELVE: You Are Not Alone (1995) vs. Music (2000)

The final round, and what a way to finish things off. Michael delivers a classic ballad of his own with “You Are Not Alone” that even an icky video with a semi-clad Michael and his then-wife Lisa Marie Presley couldn’t mar. In “Music,” Madonna returns to doing what she does best, ordering all of us to get on the dance floor and boogie like we mean it.

Winner: It’s another tough round, but Michael takes it. “Music” is fun, but it’s really all icing and very little cake, while “You Are Not Alone” is just timeless.

FINAL SCORE: Michael Jackson = 6, Madonna = 6

Whoa. I swear, I did not pre-plan this. I actually predicted Madonna would win this showdown by a fair margin, as I do believe her body of work is superior to Michael’s (and pretty much anyone else’s, aside from my beloved Tori Amos). Still, I can’t help but be glad that it all ended in a draw, as the whole point of this showdown was to remember how plain awesome both Michael and Madonna were, are, and hopefully will be (looking forward to the unreleased vault of material, MJ!).

Michael Jackson Megamix

Madonna Megamix

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