Search form

Scroll To Top
Truman Says

Madonna's 20 Most Stylish Videos

Madonna Best Videos

Look around you, the Queen of Pop has done it all. Here, a list of her most influential videos.

20. Material Girl (1984)

A first-degree tribute to Marilyn Monroe in Gentlemen Prefer Blondes, "Material Girl" is Madonna's vow to become the next most famous peroxided icon.

19. Deeper & Deeper (1992)

Madonna dresses up like one of Andy Warhol's Factory Superstars and dances the night away at Studio 54.

18. Fever (1993)

It may not be her most memorable song, but this cut from 1992's Erotica boasts one of the weirdest videos that Madonna has ever produced. The stategically-placed lily flower seems very ahead of its time after watching FKA twigs' Hide.

17. Bedtime Story (1995)

Where Madonna decides she wants to be Bjork (the Icelandic diva actually co-wrote the song). Cue some '90s-era futurist imagery, surrealist references, and a computer-generated sunflower. With a budget of $5 million, it was also the most expensive videos ever made at the time.

16. 4 Minutes (2008)

Madge looks ageless (and super hot!) in the comeback video for her hit-and-miss album Hard Candy.

15. Borderline (1983)

Madonna gets full-on Lower East Side punk, wearing with oversized leather jackets, fishnet belly shirts, and denim vests. Rihanna definitely took notes for her "We Found Love" video.

14. Human Nature (1994)

A slick BDSM-inspired video directed by Jean-Baptiste Mondino, this is Madonna's non-apology to critics who thought she was going too far in her exploration of sexual themes (see no.2). "And I'm not sorry, it's human nature," replies the QoP.

13. Hung Up (2005)

Madonna comes full-circle with her pop masterpiece Confessions on a Dancefloor. The video is a gay crowd-pleaser: Between two ABBA samples, she stretches and flexes in neon-colored leotards, surrounded the best dancers of the moment.

12. Like a Virgin (1984)

Arguably her most iconic look ever, the cheap wedding dress customized with tons of jewelry and a "BOY TOY" belt scandalized America over and over (it worked again when Britney and Christina shared that infamous kiss with Madge at the 2003 MVAs).

11. Open Your Heart (1986)

Where Madonna introduced her career-defining pointy lingerie, designed by Jean Paul Gaultier.

10. Into The Groove (1984)

Taken from the Desperately Seeking Susan soundtrack, Madonna gives a masterclass in Downtown girl '80s fashion.

09. Like A Prayer (1989)

One of her most ambitious videos, Like A Prayer is structured like a short film tackling interracial love and religion. It also depicts Madonna at her most natural.

08. Nothing Really Matters (1999)

Madonna lets Jean Paul Gaultier's geisha-inspired designs do all the talking in this stand-out single from Ray of Light.

07. Girl Gone Wild (2012)

MDNA wasn't the club-banger we were all hoping for, but Madonna saved the day with the video for "Girl Gone Wild." In what turns out to be a gay boy's complete wet dream, Madge managed to get the four hottest male models (Jon Kortajarena, Rob Evans, Simon Nessman, and Sean O'Pry) and a group of dancers in heels to play with her. Watch it on mute.

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

Directed by her ex-husband Guy Ritchie, "What It Feels Like" was banned in several countries for showing Madonna as a reckless driver. Her killer look precedes the movie Drive and the jumpsuit trend by over a decade.

05. Hollywood (2003)

Directed by David LaChapelle, Madonna dons her best retro drag in this semi-successful single from her equally half-baked "political album" American Life.

04. Express Yourself (1989)

Madonna's mega-budget video ($5 million dollars) features the iconic Jean Paul Gaultier costumes she wore during her Blonde Ambition tour, but also a very naked Cameron Alborzian --one of the most sought-after male models in the 1990s.

03. Frozen (1998)

Directed by Chris Cunnigham, "Frozen" is Madonna's darkest, most visually striking video. Shot in the Mojave desert, it shows her in full-on goddess mode, shifting her human form to turn into a flock of crows and a racing hound.

02. Justify My Love (1993)

Boys kissing boys and girl-on-girl action made it late-night-only viewing when it was released, and "Justify My Love" remains as provocative as it when it was released over 20 years ago. Madonna's scenes with hunky Tony Ward still makes us feel all weird in the tummy.

01. Vogue (1990)

You can't get more fashion-y than Madonna's dance anthem. Madonna brings vogueing out of the ballroom and into the mainstream, and channels timeless style icons for posterity.

Advocate Channel - The Pride StoreOut / Advocate Magazine - Fellow Travelers & Jamie Lee Curtis

From our Sponsors

Most Popular

Latest Stories

Julien Sauvalle