Madonna’s 11 Most Shocking Moments

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Shocking moments have always been part of the constant reinvention that makes up Madonna’s image. You would think she has shocked us so many times by this point that we would know better than to ever be scandalized by her again. She does it again tonight, by licensing her entire song catalog to Glee , for an all-Madonna episode. This is a big step forward for the woman who withheld à la carte downloads of her albums from iTunes for longer than The Rolling Stones. To hold us over until Madge gets the Glee treatment, let’s trip back through her career and relive some of her most shocking moments.

11. Her 47-year-old thighs in the video for “Hung Up”

If there is no rest for the wicked, then Madonna’s thighs have been very, very wicked. We all knew when this video was released that Madonna was sneaking up on 50. We did not know she was sneaking up on a career as a secret agent with thighs that kill.

10. Vanilla Ice turns up in Sex

There is no getting around Madonna’s strange taste in men, but this takes the cake. Sadly, Robbie Van Winkle didn’t make the Sex image montage of shock as an ironic joke. The two were really dating. This moment alone transforms Sex from pop-culture shock into embarrassing junior-high yearbook.

9. Flashing the MTV VMA audience. Twice.

Never one to keep her skirt down, Madonna has the honor of being the only artist to flash the MTV VMA audience twice: once accidentally during her inaugural 1984 performance of “Like A Virgin” and a second time on purpose with 1990’s Marie Antoinette-themed performance of “Vogue.”

8. The Malawi adoption scandal

It is lovely to think that Madonna went to Malawi to support the struggling African country, met and fell in love with the baby David, and adopted him into her life of privilege. Let’s just hope that the next orphan doesn’t have living parents or come from a country with dubious adoption laws that require a million dollar payout.

7. And the Golden Globe goes to…Madonna?

Yes, for Evita. And she beat out Frances McDormand, Barbara Streisand, Debbie Reynolds, and Glenn Close.

6. The various Letterman transgressions

What is more shocking to you, the appearance with Sandra Bernhard in which they pretended to be lesbians, the F-bomb-laden 1994 appearance, or that she came back again to make it up and play good girl?

5. Becoming a record-breaking touring artist

In striking a new blow for the continuing relevance of female pop stars and proving the Veblen Effect does exist, Madonna broke the record for top-grossing female tour EVER twice in the 2000s: once with her Re-Invention tour and again with the Confessions tour. And she did it while playing a minimal amount of markets with crazy-high ticket prices (topping out at $350). Oh, and she was strapped to a mirrored cross at the time. It is very, very impressive.

4. The Madonna/Britney kiss

You knew Madonna was going to have to put a stop to the rumors that Britney was the new Madonna. This kiss was the ultimate marker of the two merging forces and Madonna’s way of reminding everyone that Britney was just the sexy girl-come-lately. It seems like someone else might have been there too, but we’ll never know — it has been lost in the buzz of two blondes Frenching.

3. Pissing off Pepsi

The cola giant has a long history of sponsoring pop stars in order to bribe the giant chunk of the public who are ardent Coke supporters to give the ultra-cool Pepsi a try. They bit off more than they could chew in 1989 when they created a two-minute Madonna commercial set to her new single “Like A Prayer.” When the song’s accompanying music video was released and Pepsi got a look at M. kissing a black Jesus, the soft drink giant realized they were just not that cool and dropped their sponsorship immediately. Madonna reportedly kept all the money.

2. The Sean Penn wedding

Once upon a time, paparazzi did not fly over celebrity weddings to try and get pictures. They didn’t go rogue and played nicely with studios, record labels, and publicists. That all changed one sweet day in Malibu, back in 1985, when the paps attacked and Sean Penn attacked back— by firing his gun in the air at them. Where was Madonna? Laughing hysterically.

1. She’s still Madonna

For the last decade, journalists and other stars alike have been trying to grab the title the next Madonna. From Britney and Christina to Miley to Rihanna to Lykke Li. The problem is the original Madonna refuses to go down. You better watch your back, Gaga.