George Michael's 'Freedom! '90' and the 20 Super-est Supermodel Music Videos of All Time

·Editor in Chief, Yahoo Music

A quarter-century ago, reformed and reluctant pop star George Michael proved that his decision to no longer appear in his own music videos was a wise one indeed. After all, who even noticed that the ex-Wham! man and his faded “Faith” denim were M.I.A., when fashion elite like Naomi Campbell, Linda Evangelista, Tatjana Patitz, Christy Turlington, and Cindy Crawford were on MTV’s small screen?

The David Fincher-directed “Freedom! ‘90” became an iconic and game-changing music video immediately upon its Oct. 30, 1990 release. While it wasn’t the first music video to feature supermodels, and it was far from the last (some modelicious vids this year have starred new-generation fashion plates like Karlie Kloss, Gigi Hadid and Taylor Swift’s squad), 25 years later it’s still the supermodel video by which all supermodel videos must be judged.

So, yes, spoiler alert: “Freedom! '90” tops our celebratory list of the best supermodel music videos of all time. Which other girls on film made the cut? Get ready for their close-ups below.

20. Jay Z feat. Pharrell, “Change Clothes” (2003)

The Rocawear tycoon cast the ubiquitous Naomi Campbell (along with Jessica White, Liliana Dominguez, and America’s Next Top Model alum Jade Cole) for this sleek, sexy runway romp.

19. Beyoncé, “Yoncé” (2014)

Inspired by “Freedom '90,” Bey recruited new-school It-Girls Chanel Iman, Jourdan Dunn, and Joan Smalls for this glamorous-but-gritty clip. The models almost upstaged their employer (especially when Smalls, in an unscripted moment, licked Beyoncé’s bosom!), but Jay Z’s wife was still the queen of the covergirls in this one.

18. The Cars, “Drive” (1984)

Paulina Porizkova was only 19 years old when she met her future husband, Ric Ocasek, during the making of this video. Ocasek was 35 and married to another woman at the time – and that, combined with this dark video’s breakup storyline and mental-ward set, certainly didn’t seem like a promising start to their relationship. But the pair married five years later in 1989, and they’re still together today.

17. Bon Jovi, “Please Come Home for Christmas” (1995)

Jon Bon Jovi fulfilled many red-blooded males’ ultimate Christmas fantasy by canoodling under the tree with the decade’s ultimate pinup girl, Cindy Crawford. Their onscreen chemistry was a red-hot as Rudolph’s nose, but this was all a bit of Christmas pantomime: Jon’s been married to his high school sweetheart since 1989.

16. Michael Jackson, “In the Closet” (1991)

MTV regular Naomi Campbell showed off her crazy-toned thigh muscles and spoken-word skills in this steamy, sepia-toned video directed by Herb Ritts. While “In the Closet” was originally intended to be a duet between Michael Jackson and Madonna, and the recording’s spoken vocals were first performed by Princess Stéphanie of Monaco, Campbell re-recorded the vocals herself for this video. Naomi really needs to reprise this song with Bryshere Y. Gray on Empire!

15. Yeah Yeah Yeahs, “Sacrilege” (2013)

This seemingly Scarlet Letter-inspired epic, one of 2013’s best, starred scarlet-haired British model-turned-actress Lily Cole as wanton woman who pays dearly for her sins of the (freckled) flesh. Her performance was startling. If music videos could be eligible for Oscars, she would have been a shoo-in for a nomination.

14. Guns N’ Roses, “November Rain” (1992)

Axl Rose and his model girlfriend Stephanie Seymour (who also starred in GNR’s “Don’t Cry”) never married in real life, but thanks to this overblown production (one of the most expensive videos ever made), we all got to see what their literal $1 million dream wedding might have looked like. “November Rain” still doesn’t make much sense after 23 years of repeat viewing – Why does Slash leave the little white church to play a random guitar solo in the middle of the desert? Why do the reception guests completely lose their minds the minute it starts to rain? Why did Gilby Clarke attempt to act? – but Seymour’s gorgeous, garter-flashing mullet dress is everything.

13. Billy Joel, “Uptown Girl” (1983)

In an early example of trophy-girlfriend video casting, Joel cast the 1980s’ top model, Christie Brinkley, in the titular role here. The two were married from 1985 to 1994, but it was later revealed that the song was inspired by another '80s model: Joel’s previous girlfriend, Elle Macpherson. (Billy Joel certainly has a type!) In 2001, British boy band Westlife remade the song and cast yet another veteran model, Claudia Schiffer, in their accompanying video.

12. The White Stripes, “I Just Don’t Know What to Do With Myself” (2003)

This Burt Bacharach/Hal David classic was introduced to the alt-rock generation by Kate Moss, who looked decidedly un-waif-life writhing on a pole in the black-and-white video. Moss is an even harder-working video vixen than Naomi Campbell, appearing in additional music videos for Marianne Faithful, Primal Scream, Paul McCartney… and Johnny Cash.

11. Johnny Cash, “Delia’s Gone” (1994)

For the Man in Black’s fourth version of this classic murder ballad (this one appeared on his seminal comeback album American Recordings), he controversially cast Kate Moss as the song’s eponymous victim, Delia Green (who in real life was African American). The video was deeply disturbing, with Moss portraying a corpse that Cash buries in an open grave, and MTV refused to air it until a particularly explicit dirt-shoveling shot was edited out. But Moss’s exquisite corpse performance was almost as convincing as Kim Basinger’s in Tom Petty’s “Mary Jane’s Last Dance.”

10. Bryan Ferry, “You Can Dance” (2010)

Almost every Bryan Ferry or Roxy Music album cover has featured a supermodel (the one from which this single is taken, Olympia, actually featured Kate Moss), so it’s no surprise that models would star in Ferry’s videos, too. Look closely and you’ll spot an 18-year-old Cara Delevingne swaying sexily to the Bryan’s beat here. Two years later, Ferry and Delevingne reunited for an S Moda magazine fashion shoot inspired by Ferry’s relationship with '70s supermodel and Roxy Music Siren cover model Jerry Hall.

9. Warrant, “Cherry Pie” (1990)

This is either the best video of all time, or the worst. Maybe it’s both. But it’s the video that introduced Warrant’s Jani Lane to his future wife, swimsuit model and Star Search champion Bobbie Brown. For a while, the two were the It-Couple of the hair-metal era, so this vid deserves a spot in the MTV history books.

8. Hot Chip, “Night & Day” (2012)

Actor Terence Stamp and comedian Reggie Watts also made memorable cameos here, but it was gap-toothed goddess Lara Stone – playing a spaceship captain in a seriously fierce, pointy-shouldered astro-girl uniform – who stole the show in the U.K. electropop duo’s campy vid.

7. Fountains of Wayne, “Stacy’s Mom” (2003)

Inspired by Fast Times at Ridgemont High and sounding vaguely like the Cars (whose “Moving in Stereo” soundtracked that film’s famous pool-fantasy sequence), FoW reimagined Phoebe Cates’s Fast Times character as the ultimate MILF – portrayed by bombshell model/Rod Stewart ex-wife Rachel Hunter. Hunter was 34 at the time, and she proved she very much still had it going on.

6. Kanye West, “Runaway” (2010)

This ambitious and elegant mini-movie, the original version of which was 35 minutes long, starred model Selita Ebanks as a phoenix named “Griffin” that West rescues in the woods and attempts to acclimate to the human world via some sort of ballet-themed banquet. West reportedly wanted Ebanks to appear in the nude for the entire video, but she refused, which was probably a good thing – she’s a model, after all, so she looks pretty amazing in clothes.

5. George Michael, “Too Funky” (1992)

Michael almost outdid “Freedom '90” with this high-gloss, high-glamour, high-camp catwalk opus, which featured direction and costuming by Thierry Mugler and cameos by models Tyra Banks, Eva Herzigova, Nadja Auermann, “Freedom '90” veteran Linda Evangelista, and others. Michael made a small appearance this time as a cameraman, but all eyes were on the models, particularly Tyra Banks, who smized up a storm in a barely-there beaded Carnivale bikini, and Emma Sjöberg, who wowed in two amazing, futuristic metal-on-metal ensembles about 15 years before Lady Gaga would come up with similar looks.

4. Robert Palmer, “Addicted to Love” (1985)

Palmer’s model-minded music video series, which began 30 years ago with “Addicted to Love” and continued with “I Didn’t Mean to Turn You On” and “Simply Irresistible,” arguably comprises some of the most memorable and mimicked imagery in MTV history. Palmer’s backing “band members” – four nearly identical, raven-haired, Nagel-painting beauties sporting bodycon bandage dresses, slicked-back hair, scarlet pouts, and blank, copiously kohl’d eyes as they mimed along on musical instruments – became instant video icons. They’re not as well-known as some of the other women on this list, but Julie Pankhurst, Patty Kelly, Mak Gilchrist, Julia Bolino, and Kathy Davies have forever earned their spots in the annals of pop culture. (Watch them tell their story here.)

3. Duran Duran, “Girl Panic!” (2010)

Duran Duran’s passion for fashion reached its artistic high point when – in a rather George Michael-esque move – they recruited superstars from the golden era of supermodeling to portray them in this gender-bending video. Glamour girls Naomi Campbell (yes, her again!), Eva Herzigova, Cindy Crawford, Helena Christensen, and Duran frontman Simon Le Bon’s own wife Yasmin Le Bon took on the roles of Simon, keyboardist Nick Rhodes, bassist John Taylor, drummer Roger Taylor, and guitarist Dominic Brown, respectively. “I think that’s one of the most iconic things that we’ve done,” John Taylor told Yahoo Music last year. As for how was it decided which model would play which band member, John said, “I think Naomi was like, 'I’ll do it – but I’m singing!’ And she wasn’t wrong to say that. She was the perfect 'frontman.’ And then everybody else just sort of fell in.”

2. Chris Isaak, “Wicked Game” (1989)

Many music videos have starred supermodels, but few ever made as much of an impact as this Herb Ritts-directed seaside thriller with exotic Danish beauty Helena Christensen, during which she wore little more than tighty-whiteys and a smoldering stare. The chemistry between Isaak and Christensen seemed white-hot onscreen, but the two were never a couple in real life. Christensen’s actual boyfriends have included late INXS frontman Michael Hutchence and Walking Dead actor Norman Reedus, and she’s been with Interpol frontman Paul Banks since 2008.

1. George Michael, “Freedom! '90’ (1990, of course)

In January 1990, Naomi Campbell, Linda Evangelista, Tatjana Patitz, Christy Turlington, and Cindy Crawford appeared on the cover of British Vogue. The iconic photo, shot by Peter Lindbergh, inspired Michael to ring up the five models… and the rest was MTV history. Twenty-five years later, the video still holds up – as do the gracefully aging models’ good looks, as seen in these then-&-now photos.

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