Madonna's Five Worst Videos of All Time

Photo: Courtesy of WEA/Reprise

Look, there's no disputing that Madonna is the consummate music-video artist of our time. She's an earth-mother-dominatrix-cowgirl chameleon, etc., etc. "Vogue"! "Express Yourself"! "Don't Tell Me"! But as attested by the god-awful video attached to "4 Minutes to Save the World" — another gratuitous leotard, artless room-morphing effects, skeevy cougar action with JT, that Botoxy grimace — Madge can pinch out some crappy videos, indeed. Was she pressed for time? Out of obscure artists and motifs to cleverly pay homage to/rip off? Kinda bored? With great love and admiration, we present Mrs. Ciccone-Ritchie's Five Worst Videos of All Time.

5. "True Blue" from True Blue (1986)


Die-hard fans will remember a "Make My Video" contest on MTV for the title track of album three. The winning amateur filmmakers made an inoffensive black-and-white teen-romance clip — but did Madonna's camp launch the contest to cover up the blasé video already produced? All-blue set, that Jean Harlow white-blonde bouffant, stirrup pants, Capezios, and bobby-socks-y dance moves … at least this features Debi Mazar, a Madonna pal before Sandra, Rosie, and Gwynnie horned in.




4. "Jump" from Confessions on a Dancefloor (2005)


Sure, this is a banger of a dance track and should have been a bigger hit. And the video features those gravity-defying wall-rappelling French dudes from the Nike commercial jumping (get it?) around Tokyo. But it also features Madge in the worst blonde bob wig ever and a ridiculous manga skater-girl outfit, flailing about in some studio decorated with neon Japanese signs. Enough with the Asian-fetish stuff, Maddy. Please?




3. "You Must Love Me" from Evita (1996)


This pre-death dirge was written by Andrew Lloyd Webber for the film version of Evita; apropos its bald-faced title, it was intended to harangue a Best Song Oscar nomination out of the Academy. In the quickie video, a very pregnant Madge looks about two hours away from popping out baby Lourdes. Perhaps that's why she has this pained expression on her upturned face as she hides, Claire Huxtable style, behind a grand candelabra-bedecked piano, a solemn cellist behind her, and film clips galore to — futilely! — distract us.




2. "Me Against the Music," with Britney Spears, from In the Zone (2003)


Just in case you forgot, Brit helped Madonna lower her standards a full five years prior to ex-boyfriend Justin Timberlake. That VMA kiss was silly, but at least it was vaguely exciting. 'Tis not the case with their expensive-looking video collaboration, an awkward mash-up of their not-so-complementary dancing styles and a nonsensical narrative involving a voyeuristic club/mob front, M as a Dietrich-ish madam with a cane and monocle, and pre-bananas Britney as a spunky ingénue in a tie and brassiere. Maybe Madonna shouldn't play with others.




1. "Dear Jessie" from Like a Prayer (1989)


Everybody knows that Madonna was feeling wistful after her divorce from Sean Penn — it manifested itself in this unclassifiable piece of whimsy about fairies, mermaids, falling stars, etc., reportedly dedicated to a niece. It's sweet to think of a post-split Madonna pining away for kids of her own. But the accompanying, long-forgotten live-action-with-animation video, with anthropomorphized teapots and Aunt Madonna–as–Tinkerbell visiting a blonde little girl at nighttime, will haunt your dreams.
—Justin Ravitz