Stop The Presses!

Most Memorable Madonna Moments: 21-25

Lyndsey Parker
Stop The Presses!

Madonna's milestone 50th birthday is four days away, so it's not too late to pick up a present for her. But what do you get the Woman Who Has Everything? A pointy cone bra? Nope, she's got one of those. A cute Malawian orphan? She has one of those too. A Rock And Roll Hall Of Fame award? Sorry, that's covered. A 10-years-younger hot husband? She's got one of those as well--unless you believe all those divorce rumors.

Yes, Madonna is a woman who has truly done, seen, and bought it all. Which is why it wasn't at all difficult coming up with yet five more items for this ongoing list of her top 50 biggest moments. Enjoy!

21) "Ray Of Light" Lights Up The VMAs
One might have predicted that, after (in)famously kicking off the first annual MTV Video Music Awards in 1984, Madonna would only be invited back a whopping 14 years later as some sort of special guest, wheeled out to receive some token, backpatting, lifetime-achievement accolade. But no. In 1998, her kinetic quickcut video epic "Ray Of Light"--the title track from her most critically lauded album to date--swept the VMAs, winning Best Female Video, Best Choreography, Best Direction, Best Editing, and of course, Video Of The Year. Here's her typically history-making performance from the ceremony, back when she was in her Middle Eastern henna-painting phase and was for some reason employing Lenny Kravitz as her guest guitarist:

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22) She'd Like To Thank The Academy
While it may not seem so shocking now in light of Three 6 Mafia recently winning an Oscar for "It's Hard Out Here For A Pimp," it was a little bit of a surprise back when Madonna's Dick Tracy theme "Sooner Or Later" (penned by Stephen Sondheim) won the Best Song honor at the 1991 Academy Awards. Here's Madonna's Oscar-worthy, old-Hollywood-style performance (although most people probably more vividly remember her odd-couple Oscar date that evening, Michael Jackson):

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23) Madge Gets A Makeover
Although much ado has been made about Madonna being "chubby" in her early, original, rolling-on-the-floor era, before she discovered power yoga and Gunnar Peterson, let's face it: MADONNA WAS NEVER FAT. But her transformation in her 1986 "Papa Don't Preach" video was still startling. Aside from her new platinum crop and retro-pinup glamour look, Madonna's once-curvy, lightly babyfat-padded body was now a lean, mean, muscular machine. Her famously soft (and oft-exposed) stomach was now a washboard-like wonder, her arms resembled Linda Hamilton's, and her cheekbones were suddenly surprisingly prominent. After a couple of years of establishing her "Boy Toy" image, this was Madge's first major makeover--and the obviously the first of dozens to come. And after this video she only became more and more toned, proving that even the most ordinary girl from Detroit can become a superbuff fitness queen with 24-hour access to the right trainers and personal chefs, not to mention a whole lot of blonde ambition:

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24) She Gives Good Face In Her "Vogue" Video
Vogueing--a highly stylized type of dance in which participants execute a series of supermodel-like poses--was pretty much an underground club-kid phenomenon in the late '80s/early '90s. Until, of course, Madonna popularized it. Suddenly, everyone was striking a pose:

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25) Madonna's VMA Tribute Is Such A Drag
A year after her "Ray Of Light" VMA sweep, Madonna returned to the MTV Video Music Awards in 1999 as a presenter. And so did a bunch of Madonnabes, all dressed up as different iconic Madonna incarnations. It's hard to imagine a more fitting homage to Madge's fashionable career:

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Come back tomorrow for moments 16 through 20!

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