Madonna’s Top NSFW Moments

Flashing her nipple and bum are pretty tame compared to some of Madonna's most controversial acts.

When you build your career on constant shock-and-aw-nah-she-didn’t stunts, when it comes to something as mundane as flashing some skin, well, you can understand if we’re not freaking out.

But, even though she’s burned crosses, hitchhiked nude, simulated more sex on stage than most of us will ever have in real life and pissed off the Vatican for decades, people could not get enough of Madonna’s latest attempts at outrage over the past week.

After first exposing her nipple 
 during a show in Istanbul, the 53-year-old pop icon dropped trou and gave fans in Rome a shot of her taught, toned full moon 
, leaving some to wonder: what’s next?
It was just the latest in a career-long series of outrageous moments that have helped Madonna grab headlines and eyeballs for more than three decades. Here’s a look at five of Madonna’s most controversial career escapades.

Molly folly: At March’s Ultra Music Festival in Miami Madonna drew the ire of EDM star deadmau5 
 when she asked the crowd if they had “seen Molly” The seeming wink-wink nod to the drug ecstasy angered Deadmau5, who slammed the singer for seemingly promoting drug use.

Cross to bear: Though now a follower of the Jewish mystical sect of Kabbalah, Madonna was raised Catholic and has spent her career exorcising her religious demons. On her 2006 Confessions Tour she pissed off the Vatican when she spent time hanging from a mirror cross and wearing a crown of thorns during “Live to Tell.” Catholics were none too happy in 1989, either, when she sported stigmata and danced amid burning crosses in her “Like a Prayer” video.

Britney tonsil hockey: Just when you thought she had no outrage left in the tank, Madonna set tongues wagging once again in 2003 when she gave Britney Spears a long, tongue-filled open-mouth kiss.

F-bombs away!: Way before there were viral videos, Madge created an overnight must-see when she sat down with talk show host David Letterman, lit up a stogie and proceeded to drop the f-bomb more than a dozen times to the usually unflappable Letterman’s surprise.

Sex manual: She launched herself into international stardom in 1984 by rolling around on the MTV VMA stage in a wedding dress while singing “Like a Virgin,” filmed the not-safe-for-TV “Justify My Love” clip, simulated onstage masturbation on her 1990 Blond Ambition tour. But Madonna was just getting started and somehow caused jaws to drop even further in 1992 when she released the “Sex” book. The three-million-plus-selling softcore pornographic book featured copious amounts of S&M play, tons of nudity and kinky shots of the singer with everyone from rappers Big Daddy Kane and Vanilla Ice to model Naomi Campbell and gay porn star Joey Stefano.

What’s your favorite controversial Madonna moment? Let us know in comments below.

Often guilty, never convicted. 15 years behind bars at MTV News.