25. MADONNA PUSHES HER OWN BUTTONS
Her Madgesty's hyphenate could easily read ''singer/actress/pisser-offer of the powers that be.'' And on the massively successful Blond Ambition tour in 1990, Madonna's antic including simulated masturbation on stage angered Pope John Paul II and the Vatican, who publicly condemned the singer's unholy performance. On the Canadian leg of the tour, Toronto police even threatened to arrest the Material Girl for indecency. In response, she cheerfully included ''the fascist state of Toronto'' in her preshow prayers (as captured in the 1991 tour doc Truth or Dare) and refused to alter a thing.
CAREER IMPACT: POSITIVE The papal disapprobation only enhanced her taboo-taunting persona. The same year, she released a greatest-hits collection, as well as a little single called ''Vogue.''
Image Credit: Duncan Raban/Retna
From Madonna to Pee-wee, Lindsay Lohan to Britney Spears (and no, none of them made it to No. 1), we count down the most shocking celebrity moments of the past 20+ years