27. The king and queen of pop attend the Oscars together(01 of17)
Open Image ModalMarch 25, 1991Remember that time the two biggest pop stars on the planet dated? It's easy to forget since it only lasted one week. But it hit mass-chaos status when the Madonna brought Michael Jackson as her date to the Oscars, where she performed that year's Best Original Song honoree, "Sooner or Later." (credit:Getty Images)
26. Malawi adoption(02 of17)
Open Image Modal2006Madonna's adoption of Malawian infant David Banda Mwale doesn't seem like a likely entry for a list of controversial moments, but naturally even it came with a contentious flavor. The singer attracted backlash from the country's government when her request to adopt David resulted in a waiving of Malawi's ruling not to allow foreign adoptions. Madonna has since adopted a second Malawian child, Chifundo James, whose name was changed to Mercy. (credit:AP)
24. "American Life" video takes it down a notch(03 of17)
Open Image Modal23. "Erotica" album(04 of17)
Open Image ModalOct. 25, 1994Madonna's alter ego, Mistress Dita, was in full swing on the "Erotica" album, a sexually charged ode to genital liberation. In addition to the title single, whose video was banned from networks, "Deeper and Deeper," "Fever" and "Bye Bye Baby" were all provocative pop hits. The singer's next album, 1994's "Bedtime Stories," continued her sexual track.
22. Marriage to Sean Penn(05 of17)
Open Image ModalAug. 16, 1985Madonna upped the ante as a tabloid fixture by marrying Hollywood bad boy Sean Penn. She dedicated her third album, "True Blue," to the actor, but the pair divorced in January 1989. (credit:Getty Images)
21. Lady Gaga is "reductive"(06 of17)
Open Image Modal19. "What It Feels Like For A Girl" video banned(07 of17)
Open Image Modal18. Puerto Rico condemnation(08 of17)
Open Image ModalDuring the Puerto Rico stop on her "Girlie Show" world tour, Madonna rubbed the country's flag between her crotch and received official condemnation from the nation's congress. (credit:Getty Images)
17. "Erotica" days recalled in "Girl Gone Wild"(09 of17)
Open Image Modal15. The sexual era is announced via Interview(10 of17)
Open Image ModalJune 1990This one speaks for itself.
14. John McCain is Hitler?(11 of17)
Open Image ModalAug. 23, 2008During the opening stop on her Sticky & Sweet Tour, Madonna compared Republican presidential candidate John McCain to Hitler during a video montage. (credit:PA)
13. Religious groups crucify "Live to Tell" performance(12 of17)
Open Image ModalMay-September 2006German prosecutors threatened to sue Madonna after she performed "Live to Tell" while standing on a cross and wearing a crown of thorns on her "Confessions" Tour.
11. "Body of Evidence" nabs NC-17 rating(13 of17)
Open Image ModalJanuary 1993The sexually provocative "Body of Evidence" received an NC-17 classification upon its completion, but its theatrical release was softened enough to earn an R rating. The video release retains the initial version.
10. The cone bra(14 of17)
Open Image ModalApril 1990Madonna's cone bra has taken on many iterations, including during her recent "MDNA" Tour. Its genesis came at the hands of Jean-Paul Gaultier during the Blonde Ambition Tour, sparking backlash as well as numerous copycat versions. (credit:Getty Images)
9. Nude Penthouse photos(15 of17)
Open Image ModalSeptember 1987Having already caused an uproar in 1985 when Playboy and Penthouse published nude photos from 1978, more controversy arose when Penthouse featured another set of naked gems.
6. "Like a Prayer" video's burning crosses infuriates religious communities(16 of17)
Open Image Modal1. "Sex"(17 of17)
Open Image ModalOct. 21, 1992Nothing is Madonna's illustrious career is more notorious than "Sex," the coffee-table book that was loaded with erotic photos, including multiple nudes of the singer engaged in graphic sexual acts. The book remains one of the most sought-after out-of-print materials.