Stop The Presses!

Most Memorable Madonna Moments: 41-45

Lyndsey Parker
Stop The Presses!

Our daily countdown of the top 50 highlights and lowlights in Madonna's career--leading up to her 50th (yes, 50th!) birthday on August 16--continues apace today with Madge moments 41 through 45. If you don't see your personal favorite memories on this list yet, please refrain from posting angry messages on our board, because there's a strong chance that they'll show up on the list somewhere between spots 1-40. But do feel free to start sharing your own favorite Madonna memories on the board below, or just post your birthday well-wishes to the hottest half-centenarian ever!

41) Madonna And Missy Elliott Fall Into The Gap
M&M, together at last! Two of the music biz's most iconic and individualistic hitmakers, Madge and Missy became bluejean babies in 2003, when they teamed up for a memorable Gap commercial. They both looked fly, and Missy sounded so-addictive rapping on Madonna's "Hollywood"/"Into The Groove" mashup...but Madonna wasn't very sportswomanlike when demonstraed her advanced yoga moves while poor Missy toppled to the floor. That Madonna, always a showoff:

42) Her Estranged Brother Christopher Pens Memoir
In 2008, Madonna's brother Christopher Ciccone authored the oh-so-creatively titled Life With My Sister Madonna, in which claimed that his big sis once passionately kissed Gwyneth Paltrow and that she loves herself and her career more than she loves her husband, among other revelations. "I hope that it is Kabbalah's lesson that she is not the center of the universe," he wrote. Ouch. Perhaps unsurprisingly, he also admitted that he and Madonna are no longer close. Hmmm...maybe Madonna should record a remake song called "Brother Don't Preach":

43) Madonna Puts The "M" In "H&M"
Although Madonna's line of nonbreathable, synthetic-material tracksuit jackets for the discount fashion chain H&M weren't exactly as stylish as the couture hanging in her own closet--we would have preferred a line of cone bras or rubber jelly bracelets, really--Madonna still managed to make her cheapo clothes look good:

44) Weird Al Yankovic Releases "Like A Surgeon"
There an old saying in showbiz: You haven't really "made it" until you've been parodied by Weird Al. So when the bespectacled song-comic geek rolled around seductively on a hospital floor during his video sendup of "Like A Virgin," it was official: Madonna was now a bona fide A-lister:

45) She Monkeys Around On The Oscars
When Madonna's longtime buddy/sparring partner David Letterman (who will reappear on other lists later this week, don't you worry) hosted the Academy Awards in 1995, he gathered a bunch of famous friends for a comical clip making fun of his bit part in the straight-to-video pirate comedy Cabin Boy. Madonna was among these friends, and with her five-second cameo she managed to upstage pretty much everyone--including probably whoever actually won Oscars later that night:

Come back tomorrow for Madonna moments 36-40!

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