TOURNAMENT ARCHIVE: Madonna

Kneel to Like a Prayer

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In the summer of 1958, on the continent of North America, three supernovas of North American popular music would be born. Now, on the 60th anniversary of this celestial episode, we at Choon Group celebrate the divine creations of these pop gods by launching 60 each of their greatest creations into glorious competition, allowing we mere mortal stargazers to decide the fates, and declare which of their classic jams shall henceforth be known as the Most Legendary Song for each of this trio we call, The Legends of '58!

The Championship Round of our Madonna Tournament was won by the emotional, the sensual, the dramatic, the controversial "Like a Prayer," which faced its first real battle in its five matchups against the beloved black and white of "Vogue," but still pulled in a solid majority of voters, scoring a 56.8% to 43.2% victory. We hereby declare it Madonna's Most Legendary Song and raise a cold Pepsi-Cola to its enduring delights. Big thanks to the many Madonnaficianados (TM) and loyal Choon Group readers who weighed in with their life-giving clicks over three weeks of competition. Visit the links below to see how each successive round shook out, with breakdowns of every individual matchup:

ROUND ONE RECAP
ROUND TWO RECAP
SWEET SIXTEEN RECAP
ELITE EIGHT RECAP
FINAL FOUR RECAP

You can reminisce with the full field of 60 songs, a career-spanning and creatively curated box set's worth of classics by Madonna Louise Ciccone (Born August 16, 1958 in Bay City, Michigan) via our Spotify playlist and Bracket Breakdown Podcast below.

The 60 competing tunes were divided into four ranked brackets of 15 songs, each named after one of Madonna's more memorable cinematic adventures. Each song's final overall ranking is indicated in parentheses after the title, determined by 1) how far they made it in the tournament, 2) the percentage of votes they earned in their final round, and 3) the higher seeded song breaking any ties after 1 and 2, is indicated in parentheses after the title. Clicking the title of each song will take you to its official music video.

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1. Into the Groove (4th) Written by Madonna for the 1985 Susan Seidelman movie Desperately Seeking Susan in which she appears, this was not technically a single in the US despite its radio and MTV ubiquity, but was named by Billboard as Dance Single of the Decade. And it is wonderfully '80s.


8. Nothing Really Matters. (33rd) This tasteful piano-driven dance groove, a 1999 deep single from Ray of Light, comes from her fruitful collaborations with William Orbit and Marius De Vries.

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9. Dress You Up. (32nd) A #5 hit in 1985 and the final single from Like a Virgin, this teen-pop bop you should totally Carlton to was oddly included on the PRC’s “Filthy 15” list of songs exemplifying smut and moral turpitude, perhaps because Tipper Gore wanted something by Madonna on the list and “Like a Virgin” was too on the nose?


5. La Isla Bonita. (17th) The final single from True Blue was a #4 hit in 1987. Its all-synth orchestra adds to the fine Spanish cheese (manchego?), including that hilarious “time for siesta” bridge. This song will never not remind me of Eric Cartman’s trip to Casa Bonita.

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12. I’ll Remember. (55th) One of her many movie soundtrack hits, this was the theme to the 1994 Joe Pesci/Brendan Fraser vehicle With Honors and found her cleaning her image up to adult contemporary after the naught trifecta of her album Erotica, her coffee table book Sex and role in erotic thriller Body of Evidence. I kind of like its sweet valedictory tone now, though I’m sure I hated it in ‘94 when I was actually graduating high school.


4. Secret. (12th) Choon! This lead single from Bedtime Stories went to #3 in 1994, and started her love of acoustic strummies, taking her in an R&B direction courtesy of producer and co-writer Dallas Austin, known for his work with TLC.
 
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13. You’ll See. (56th) Another toning-down period, as in 1995 Madonna released an all-ballads compilation called Something to Remember. This collaboration with schlockmeister David Foster was a #6 chart success. More Spanish guitar to go with a defiant tone--”You’ll see...you’ll all see!”


6. Deeper and Deeper. (22nd) Much to unpack here on this #7 Erotica hit and coming-out anthem: Snare rolls. Orch hits. Lyrical references to The Sound of Music and her own “Vogue.” the familiar Madonna theme of struggling with parental influence. And a flamenco breakdown?

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11. What It Feels Like for a Girl. (45th) The final single from 2001’s Music LP challenges men to reevaluate gender roles, and features a spoken intro by Charlotte Gainsbourg from the 1993 British drama The Cement Garden that inspired Madonna’s lyrics.


3. Open Your Heart. (5th) A big #1 hit from 1986 with a memorable Jean-Baptiste Mondino minor-corrupting peep show video, featuring a nice rhythm track and some “Sussudio”-style horns.  Also the tune in which we learn Madonna is a really fast runner.

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14. Oh Father. (53rd) Oh, father. One of a few Madonna songs to get a David Fincher-directed video, this Like a Prayer single goes in for autobiographical detail--the death of her mother at age 5 and her fraught relationship with her father. This had been a skipper for me in years past but I’ve come around to it preparing the brackets. 


7. Hung Up. (21st) This one is Seth’s jam, which made me give it another chance despite my strong ABBA-aversion (this samples the Swedes’ “Gimme Gimme Gimme”), and I found I quite liked much of 2005’s Confessions on a Dance Floor of which this spirited kiss-off was the lead single and a #7 hit.

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10. (43rd) Drowned World/Substitute for Love. The opener of the Ray of Light album, inspired by the birth of her daughter,  gives us delayed gratification with its ambient intro and slow build-up. Use of a string sample lead to songwriting credits for Rod McKuen, and Anita Kerr of Mexicali Singers fame.


2. Borderline. (10th) Big choon, major earworm. This enduring jam was her first Top Ten hit in 1984, as she belts disco vocals over bubblegum synthpop, and breaks it off with a sleazy photographer in the video while wearing a big silly hat.

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15. Bitch I’m Madonna. (44th) Here’s the lead single from LP #13, 2015’s Rebel Heart, in which 56-year old mother of six Madonna Ciccone revels in wanton hotel pool party destruction, aided and abetted by Diplo and Nicki Minaj.
 

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1. Like a Prayer. (1st) Massive #1 hit and title track from her 1989 album, the controversy surrounding the pop/gospel tune’s video, which featured some sexually and racially-charged imagery, got her dropped by Pepsi (though she got to keep the check). It all seems pretty quaint now. Choon holds up.


8. Take a Bow. (31st) It’s a tough draw for this Babyface collaboration from Bedtime Stories that stayed at #1 for 7 weeks in 1994. The one with the bullfighter video, it’s a classy if sappy orchestral ballad with laid-on-thick showbiz imagery.

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9. True Blue. (39th) Title track from her 1986 LP inna doo-wop stylee was a #3 hit, remembered by some for MTV’s “Make My Video” contest in which aspiring filmmakers sent in lots of pretty bad attempts at promo clips. Watching the final-vote special with my sister back then, hearing this song on repeat, has forever doomed it for me.    


5. Bedtime Story. (25th) Cool in multiple senses, Björk wrote this minimalist electronic meditation, produced by Björk’s “Human Behaviour” collaborator Nellee Hooper. Björk later rewrote it as “Sweet Intuition,” completely changing the lyrics and thus losing the gem, “Words are meaningless/Especially sentences.” P.S. Its video is on permanent display at MOMA.

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12. Everybody. (37th) Her first-ever single from October of 1982, a simple disco/new wave thing whose demo she pushed as she came up in the New York club scene, eventually getting her signed to the Sire Records arm of Warner Brothers, with whom she recorded for 25 years.


4. Crazy for You. (16th) Perfect middle school slow dance vibes from her first #1 hit ballad, taken from the soundtrack of 1985 Matthew Modine flick Vision Quest. Her lower register pleases on the verses of this one, produced by her frequent early days collaborator John “Jellybean” Benitez.

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13. Causing a Commotion. (52nd) A #2 hit from the movie this bracket’s named after, it finds her pumping out material for the soundtrack of the Griffin Dunne-costarring screwball comedy and coming up with a major “Into the Groove” retread.


6. Love Song. (47th) Her only collaboration with fellow Legend of ‘58 Prince, our selection committee buoyed this Like a Prayer album cut with our first tournament fresh in mind. It’s definitely a purple production--check out the drums, bass and vocal harmonies on this slinky relationship funk. She’d revisit the “Time goes by so slowly” lyric on “Hung Up” 16 years later.

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11. Who’s That Girl. (27th) A #1 hit single in 1987 from a massive flop movie--that’s a neat trick from our señorita mas fina. Not to keep baggin’ on the Who’s That Girl soundtrack, but this has a strong scent of “La Isla Bonita” from the previous year.


3. Like a Virgin. (13th) Parodied by Weird Al, writhed-around to at the VMAs, and banned from getting played at recess by my 4th grade teacher Mrs. Weinbrenner, it’s her first #1 hit, an iconic superstar-making moment from 1984. Lots of cheese here, but produced by Nile Rodgers, so I’m still bobbin’ my head.

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 14. Sorry. (42nd) The second single from Confessions on a Dance Floor, around the time she stopped getting automatic radio play, is still a quality filter-heavy dancefloor kiss-off. The Pet Shop Boys gave it a remix.


7. Frozen. (24th) Frequent collaborators Patrick Leonard and William Orbit brought their respective pop and electronic sensibilities to this #2 hit, the lead single from 1998’s Ray of Light. It’s got a very cool Chris Cunningham CGI-effects video, but the song has aged a little musical theatre for my taste.

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10. Angel. (51st) A #5 hit from Like a Virgin in 1985, it’s got that peppy Pointer Sisters-era energy. Also, for those playing the Madonna lyrics drinking game: Catholic imagery--drink!!


2. Music. (7th) Let’s hear it for a late-career #1 smash! For Ali G and cowboy hats! Madge and French producer Mirwais made a great team on this album, and the title track from their year 2000 album still bangs, even as a bald-faced attempt at a hit. The turn of the century was a club-going period for me, and I feel pretty #blessed to have had this choon.

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15. Love Don’t Live Here Anymore. (60th) A curious case: the cover of a 1978 Rose Royce soul ballad added to the Like a Virgin album at the eleventh hour, then remixed and released as a single from the Something to Remember comp over ten years later, featuring a stylish single-take Mondino video.
 

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1. Vogue. (2nd) A #1 hit in 30 countries, a 2 million seller (6 million worldwide) that knocked Sinead O’Connor and Prince’s “Nothing Compares 2 U” out of the top spot in 1990. Seldom have canned electronic snares been used so thrillingly on the house-junior production by Shep Pettibone, as she celebrated and elevated the Vogueing dance form of the Harlem House Ball community. (Some controversy there, as she was seen to not have been properly crediting its origins, like she was going around incessantly saying “Yaaas Kween” out of context.) David Fincher on the vid again.


8. Burning Up. (46th) Second single, singed from her 1983 self-titled debut, just before she started to break big. The rock guitars in this are kinda dumb, and she rhymes “Fire” with Desire” in the first 30 seconds.

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9. Erotica. (29th) The title track from her 1992 album finds Madonna indulging in her weakness from that early-90s period, talk-singing. (“Secret garden,” anyone? Not our selection committee!) Despite it not really fitting in to radio, it was a #3 chart hit.


5. The Power of Good-Bye. (26th) This Ray of Light single was a decent success, hitting #11, but as an MOR power ballad, I have very little interesting to say about it.

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12. Die Another Day. (38th) Hell yes, Madonna gets a Bond theme! Lyrics tied to the 2002 Pierce Brosnan movie’s themes (there were themes?) of ego destruction, as well as delayed gratification, do result in the cringeworthy Sigmund Freud line, but this still kind of jams, with Mirwais back for an encore.


4. Beautiful Stranger. (15th) Another soundtrack, another spy, but three years earlier from the second Austin Powers jokefest. I remember this being ubiquitous, but it only reached #19. Nonetheless, its swingin’ 60s psychedelic pop vibe was heavily favored by our groovy committee.

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13. Keep It Together. (41st) Like a Prayer hit with something like a DC go-go beat, this propagates the message that family will cause you the most misery in life, but you'll be required to stick with them.


6. Lucky Star. (11th) Her first Top Ten hit in late ‘83 found her about to blow up with some tasty vintage “Jellybean” Benitez lite-funk. The video sees her in her classic OG “boytoy” look. Hee-yeah!

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11. Don’t Cry for Me Argentina. (54th) The only selection from the 1996 film version of Andrew fucking Lloyd Webber’s Evita (Sorry completely not sorry, Oscar-bait “You Must Love Me”), we’re highlighting the inevitable Spanglish dance remix to maximize cringe value.


3. Live to Tell. (18th) Another big #1 hit ballad which propped up then-husband Sean Penn’s 1986 film At Close Range, it’s got a dramatic mid-song dropout before the bridge, pretty crazy for radio at the time (or any time).

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14. Give It 2 Me. (49th) The second single from 2008’s Hard Candy brings in Pharrell and The Neptunes for vocals and production, which despite sounding like an updated Casio preset, actually kind of works, helped along by an oddball percussion break.


7. Rain. (19th) Another example of a (A&R-enforced?) mellowing-out after extended sexytime, “Rain” is a solid uplifting ballad and moderate success from Erotica.

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10. Material Girl. (34th) The song Madonna has said she most regrets, as it got her tagged with an unwanted media nickname and was unironically enjoyed by many a Reaganite, this #2 hit had one of early-days MTV’s most-overplayed videos, her iconic recreation of Marilyn Monroe’s “Diamonds Are a Girl’s Best Friend” number from Gentlemen Prefer Blondes. Hooks galore, including the goofy robot-voice backup dudes.


2. Human Nature. (6th) This Bedtime Stories single only reached #46, but our selection committee loves it. Madonna stayed vital in the 90s during alt-rock and hip-hop’s ascendance, and here she figures out how Madonna does hip-hop, sampling Main Source and talking some shit like an angrier, richer Salt n’ Pepa. Jean-Baptiste Mondino shepherds another great video for her (despite the cornrows).

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15. Give Me All Your Luvin’. (59th) Not a ZZ Top cover. (Unfortunately?) Lead single from 2010’s MDNA, this retro-new wave/hip-hop/cheerleader amalgam is her most recent Top ten hit, notable for guest MC M.I.A.’s Super Bowl finger.
 

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1. Holiday. (9th) Her first charting hit from 1983, this is just classic good-time post-disco escapism, Jellybean on the track.


8. Get Together. (30th) The third single from dance throwback LP Confessions on a Dancefloor, this has a lot packed into its DNA: inspired by Stardust’s “Music Sounds Better with You” and featuring references to S.O.S. Band’s “Take Your Time” as well as her own “Holiday” and “Secret.”

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9. This Used To Be My Playground. (35th) Summer 1992 #1 hit balladry from the film this bracket’s named after, this sad bastard tackles aging and regret, and yet, there’s no crying in baseball.


5. Ghosttown. (40th) The committee showed a bunch of love to this Rebel Heart single, which takes a little autotune, adds a big big chorus and adds up to a triumphant power ballad.

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12. Justify My Love (8th). Hey, a #1 hit from a greatest hits album (1990’s landmark The Immaculate Collection)--neat trick, Madonna! This one’s got everything (Stefon voice): talk-singing, a Public Enemy/James Brown trip-hop sample, Lenny Kravitz, Prince protégée Ingrid Chavez, moaning, “Wayne’s World” sketch fuel...


4. Ray of Light. (20th) New Agey sentiment met of-the-moment dance music and got the title song from her 1998 LP into the Top Five, with its ecstatically upbeat scream-along chorus.

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13. American Life. (58th) AKA, the one that almost killed her career. Maybe we weren’t being fair--it’s still got the Mirwais production and guitar strummies, and the bonkers video that got pulled does a pretty good job satirizing America’s obsession with and desensitization to violence and war. Oh but that “hotties and pilates” rap. Madonna listing off all her employees single-handedly made her 2003 American Life LP a non-starter.


6. Papa Don’t Preach. (14th) #1 smash from True Blue, this unexpected-pregnancy pop melodrama with the irresistible chorus made a teen sensation out of video co-star Danny Aiello. (See below. Please, see below.)

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11. Bad Girl. (36h) Third Erotica single, an underrated pop ballad that sees Madonna in a sad place, behaving badly after a breakup, a long long way from “Holiday, celebrate.” David Fincher on the vid again, bringing together the long-awaited screen team of Madonna and Chris Walken.


3. Cherish. (23rd) Sticky-sweet #2 hit single from Like a Prayer throwing back to but executing better the retro-pop of “True Blue” and referencing The Association, which was a band from the ‘60s that appears to have been comprised of 43 Mormons. Anyway, this “Cherish” sported a not-unhot beachy video shot by Herb Ritts.

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14. I Want You. (50th) Editor’s pick here: This Nellee Hooper-produced collaboration with Bristol trip-hop legends Massive Attack, stood out on the 1995 Marvin Gaye tribute compilation Inner City Blues, as well as Madonna’s Something to Remember. A classy updating that honors the original and suits the styles of the covering artists.


7. Don’t Tell Me. (28th) The second single from Music made it to #4, with a co-write from singer-songwriter/Madonna brother-in-law Joe Henry. This is country line dance Madonna.

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10. 4 Minutes. (48th) The lead single from Hard Candy, featuring Timbaland and Justin Timberlake reeks of perspiration without inspiration, with Madonna basically swapping in for Nelly Furtado here.


2. Express Yourself. (3rd) Big Ass Choon, kids. Part of the enormous pop culture summer of 1989, an empowerment anthem so indelible it would be ripped off wholesale 22 years later by Lady Gaga. Madonna and longtime friend/collaborator Stephen Bray blend her (sorta Cher-ish) vocals and dance rhythms to create pop perfection. Fincher on the vid one more time in our tournament, his milk-spilling Metropolis homage making things challenging for me as a developing 13-year old.

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15. Celebration. (57th) Since “Legends of ‘58” is a celebration of three great pop music icons, what better title to close us out than the tacked-on title track to Madonna’s 2009 greatest hits repackaging Celebration? (Okay, it’s not that awesome, but its Paul Oakenfold-assisted trance-lite is better than the Lil’ Wayne-featuring Rihanna ripoff "Revolver" on that collection.) Here she does that thing again where she quotes one of her earlier hits, this time “Into the Groove.”

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