From Madonna to Pee-wee, Lindsay Lohan to Britney Spears (and no, none of them made it to No. 1), EW.com count down the most shocking celebrity moments of the past 20+ years.
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.''
24. WHITNEY HOUSTON WASTES AWAY
On Sept. 7, 2001, one month after signing a $100 million record deal with Arista, Houston shocked audiences at the Michael Jackson 30th Anniversary Celebration concert with her alarmingly gaunt appearance. Speculation was rampant: Was Houston — whose prior studio album had sold a disappointing 2.8 million — anorexic? On drugs? In 2002, the singer sat down with Diane Sawyer and admitted to past drug use, but declared: ''Crack is wack.''
CAREER IMPACT: MINOR This episode was one among Houston's many career setbacks, including being fired from an Oscar performance in 2000, and a weird 2005 reality show with husband Bobby Brown. Today the singer — who arrived looking glam and healthy at a pre-Grammy party in February, and who filed for divorce from Brown last year — is recording a new album with Clive Davis.
23. KATE MOSS LOSES GIGS OVER DRUG DRAMA
In September 2005, in what some might call a career ''high,'' the waify supermodel was featured on the front page of Britain's Daily Mirror allegedly snorting cocaine. Moss' extremely lucrative fashion contracts (including H&M, Chanel, and Burberry) quickly disappeared as sponsors reacted with shock — shock! — at the spectre of drug use invading the fashion industry. (Due to lack of evidence, Moss was not charged.)
CAREER IMPACT: MINOR Following a public apology and a rehab stint, Moss reestablished a few of her old deals, and inked a number of new ones. She has also recently debuted a well-received clothing line for London's trendy Topshop.
22. O.J.'S FAKE TELL-ALL GOES BUST
On Nov. 14, 2006, Fox announced a two-part interview with O.J. Simpson, tied to the release of If I Did It, a fictional tell-all that HarperCollins exec Judith Regan gave Simpson a hefty fee to write — about the hypothetical details of how the ex-football great might have killed Nicole Brown Simpson and Ron Goldman. Within the week, a wave of protests from Fox affiliates, the victims' families, and a disgusted public drove News Corp. (parent company of Fox and HarperCollins) to cancel the bizarre endeavor.
CAREER IMPACT: MAJOR Regan was fired on Dec. 15. Meanwhile, a judge awarded the book rights to Goldman's family to help satisfy their $33.5 million civil-suit decision against Simpson, and on Aug. 14, Beaufort Books announced a deal with the family to publish the totally made-up tale: It's due out Oct. 3.
21. ROB LOWE: SEX-TAPE PIONEER
During the 1988 Democratic convention in Atlanta, Rob Lowe picked up two gals (ages 22 and 16) at a club, invited them back to his hotel, and videotaped the romp. Naturally, the home movie leaked out — and grainy footage of the Brat Packer in action made the tabloid-TV rounds. The underage girl's mom sued Lowe, but it was settled out of court, and no charges were filed. (He agreed to perform 20 hours of community service.)
CAREER IMPACT: MINOR After a brief rehab stint for alcohol addiction in 1990, the star went on to wink at the incident in his work, including the 1999 West Wing pilot — in which his character, a presidential aide, unwittingly sleeps with a hooker. As Lowe noted in 2000, ''At the height of my downfall, I was still making a million bucks a picture.''
20. COURTNEY LOVE'S BABY SHOCKER
Choosing a favorite Courtney Love scandal moment is kind of like picking your favorite Beatles record: So...many... choices! Must...stay...focused! But there is one moment Love-ologists find universally shocking. After a 1992 Vanity Fair article suggested she was knowingly using heroin while pregnant, Love denied it, insisting that she sought medical help and quit as soon as she found out. Three years later, she told Barbara Walters she only used in the first month of pregnancy.
CAREER IMPACT: MINOR On April 12, 1994 — four days after her husband, Kurt Cobain, was found dead of a self-inflicted gunshot wound — Love's band Hole released their most successful album to date, Live Through This. Today, Frances Bean is a healthy 15-year-old, but her mom (who hasn't released a new album since 2004) gets more attention for her yo-yo-ing weight than her music career.
19. ROSIE QUITS THE VIEW
O'Donnell's reign over The View ended exactly the way it should have: in a split-screen shout-off with conservative cohost Elisabeth Hasselbeck. The impassioned, uncomfortable, please-go-to-commercial-now tiff embodied everything that made O'Donnell's stay on the chatfest so riveting. For nine ratings-boosting months, the former Queen of Nice unveiled a new TV persona — now with 50 percent more liberal outrage! She feuded with The Donald, criticized national institutions from the White House to American Idol, openly discussed her gay marriage, and even held a hungover Danny DeVito on her lap.
CAREER IMPACT: POSITIVE After the blowup, O'Donnell — who had already given notice — quit three weeks early. The ongoing and intense speculation over her next move demonstrates that even an angry Rosie is an in-demand Rosie.
18. ROSEANNE'S STAR-MANGLED NATIONAL ANTHEM
When Roseanne Barr took the mound at San Diego's Jack Murphy Stadium to sing the national anthem on July 25, 1990, nobody expected an aria. But they weren't prepared for the 55-second caterwaul she unleashed, either. And they definitely didn't anticipate her final flourish, in which she grabbed her crotch and spit. The mockery left the audience in jeers, and even President Bush (the elder) called the performance ''disgraceful.'' Barr apologized, but remained defiant. ''The whole thing is a huge statement on America. The reaction more than the act,'' she later said.
CAREER IMPACT: POSITIVE That fall, Barr's landmark ABC sitcom returned for a third Emmy-nominated season, bolder and better than ever.
17. PORNO FOR PEE-WEE
Sometimes even a kids'-show host needs to sit back, relax, loosen his bow tie...and take in a triple feature of porn. On July 26, 1991, Pee-wee's Playhouse host Paul Reubens had such a night out in Sarasota, Fla., leading to his arrest for indecent exposure. (He pled no contest and paid a fine.) Save a self-mocking MTV appearance two months later (''Heard any good jokes lately?''), Reubens laid low for the next decade.
CAREER IMPACT: MAJOR Reubens' comeback with 2001's Blow was overshadowed by a second arrest in '02, after photos of nude teens were found in his L.A. home. (He pled guilty to possession of obscenity, but maintained the photos were ''vintage erotica.'') This fall, Reubens has a recurring role on ABC's Pushing Daisies, and he's also written scripts for two more Pee-wee movies.
16. DON IMUS FOULS OUT
Racist, misogynist, and homophobic slurs were not uncommon on Don Imus' nationally syndicated radio show. But when the shock jock called the Rutgers women's basketball team ''nappy-headed hos'' on April 4, the vulgarity of his words — aimed at a group of accomplished college athletes, no less — enraged the public, and made many advertisers jump ship.
CAREER IMPACT: MAJOR After MSNBC pulled its simulcast of Imus in the Morning, CBS Radio canceled the show outright. The impact may be short-lived, however: On Aug. 14, Imus reached an undisclosed settlement with CBS, and is reportedly plotting a return to radio.
15. LINDSAY'S CAR-CHASE CHAOS
Most of Hollywood saw this tipping point coming a mile away: Early in the morning on July 24, Lindsay Lohan was arrested for alleged DUI (her second in as many months), driving with a suspended license, and cocaine possession. All this came only 11 days after a 45-day stint in rehab. The 21-year-old was charged with a total of seven misdemeanors in both cases. Through a lawyer, she arranged a plea bargain on Aug. 23. She pled guilty to two counts of being under the influence of cocaine and no contest to two counts of driving with a blood alcohol level of 0.08% or higher and one count of reckless driving; two DUI charges were dropped. Lohan will serve one day in jail and 10 doing community service, in addition to completing a drug treatment program. ''It is clear to me that my life has become completely unmanageable because I am addicted to alcohol and drugs,'' the actress said in a statement.
CAREER IMPACT: MAJOR Lohan — reportedly in rehab again — saw her latest flick, I Know Who Killed Me (released three days after the arrest), open with only $3.5 million.
14. MICHAEL RICHARDS' RACIST RANT
When Seinfeld's Michael Richards took the stage at L.A.'s Laugh Factory on Nov. 17, 2006, the audience was probably hoping for Kramer-ish pratfalls and copious arm-flailing. What they got instead was a racist diatribe directed at a group of African-American hecklers. Thanks to a cell-phone camera, the tirade immediately hit the Web, earning the actor nationwide condemnation. Three days later, Richards appeared via satellite on David Letterman's show, apologizing and pledging to seek help.
CAREER IMPACT: MINOR Richards hadn't acted on screen since his eponymous sitcom was canceled in 2000. While on a spiritual journey in Cambodia last month, he told the L.A. Times that he has quit stand-up comedy.
13. MILLI VANILLI LIP-SYNCH LIE EXPOSED
The supposed curse of the Best New Artist Grammy reached its apex in 1990, when Rob Pilatus and Fabrice Morvan — a.k.a. Milli Vanilli — were stripped of the award after producer Frank Farian revealed that the two men were professional lip-synchers who hadn't sung one note on their chart-topping debut album. Apparently, 11 million fans can be wrong.
CAREER IMPACT: MAJOR The duo became a worldwide punchline — not to mention an indictment of the music industry's increasing interest in image over content. Repeated attempts to launch legitimate careers failed; Pilatus overdosed in an apparent suicide in 1998.
12. ISAIAH MOUTHS OFF — SHOOTS SELF IN FOOT
Just when you thought the drama on ABC's Grey's Anatomy couldn't get more overwrought, it did — behind the scenes. It began with an October 2006 dustup between Isaiah Washington and Patrick Dempsey in which the former allegedly referred to gay costar T.R. Knight as a ''faggot.'' The incident was close to fading from public memory until Washington dropped the f-bomb again (as part of a denial) in front of reporters at the Golden Globes in January.
CAREER IMPACT: MAJOR Even after he attended anger-management training and shot an anti-hate-speech PSA, the network told Washington in June that his services at Seattle Grace were no longer needed. In July, however, NBC gave him a five-episode gig on this fall's Bionic Woman.
11. TOM TAKES ON PSYCHIATRY
Bouncing on Oprah's couch was a little odd, but it was Tom Cruise's leap into a heated debate over the mental-health profession that really puzzled fans. In May 2005, while promoting Paramount's War of the Worlds, Cruise criticized Brooke Shields for taking antidepressants during her postpartum depression. He then tore into the Today show's Matt Lauer, calling him ''glib'' for suggesting that the ADD drug Ritalin has helped people.
CAREER IMPACT: MAJOR In August 2006, Viacom chairman Sumner Redstone ended Paramount's relationship with Cruise's production company, citing the actor's ''recent conduct.'' Cruise, now co-head of United Artists studio, will next be seen with Meryl Streep in November's Lions for Lambs.
10. MARIAH TEETERS ONTO TRL
All that Glitters, it seems, was actually fool's gold for Mariah Carey in 2001. In a surprise appearance to promote her tinselly travesty of a movie, the overworked pop tart popped into MTV's Total Request Live studio pushing an ice cream cart and proceeded to peel off her baggy T-shirt, unveiling gold booty shorts and a tank top. ''Every now and then,'' she told confused host Carson Daly, ''somebody needs a little therapy.''
CAREER IMPACT: MAJOR Glitter bombed, and Virgin Records paid $28 million to buy Carey out of her contract in 2002. Three years later, though, Carey emerged from her shame cocoon as the Billboard-topping butterfly who had the best-selling album of 2005 with The Emancipation of Mimi.
9. BRAD - JEN + ANGIE = BRANGELINA
Brad Pitt and Angelina Jolie already share the unique mutual handicap of being the world's most beautiful movie stars. So when the duo — who both had a knack for on-set romances — teamed up in 2004 for Mr. & Mrs. Smith, the gossip industry raised its alert level to red. By March 2005, Jennifer Aniston had filed for divorce from Pitt, and less than a year later — after months of playing coy — Jolie announced she was bearing Pitt's love child.
CAREER IMPACT: MINOR ''Brangelina'' became a tabloid phenom, but the new couple wisely shifted the focus to their charitable endeavors and ever-growing family (current count at press time: four). Aniston, meanwhile, emerged with copious public goodwill. All three parties continue to look very, very pretty.
8. BRITNEY'S BIZARRE BUZZ CUT
Turns out the denim dress she wore to the 2001 American Music Awards won't go down as Britney Spears' most unfortunate style decision. On Feb. 16, a visibly distressed Spears paid an after-hours visit to a Tarzana, Calif., salon. After the owner refused to shave the pop star's head, Spears buzzed it herself.
CAREER IMPACT: MAJOR Spears' increasingly erratic behavior continues (most recently when she reportedly partied topless with a music-video extra in a hotel hot tub), further complicating her custody battle with ex Kevin Federline over sons Sean Preston, 23 months, and Jayden James, 11 months. Now the public is more interested in whether the platinum-selling artist will keep her kids than if she'll stage a successful comeback.
7. DIXIE CHICKS DIS BUSH — COUNTRY GOES CRAZY
It's almost quaint, remembering when opposition to the Bush administration could be a radical statement. But when Natalie Maines of the Dixie Chicks told a London audience on March 10, 2003, that the trio was ''ashamed'' to share a home state with the U.S. president, it was the gibe heard round the world.
CAREER IMPACT: MINOR While they initially took a drubbing — their chart-topping single ''Travelin' Soldier'' vanished, and mocking the group became No. 1 with a bullet on conservative talk radio — things began looking up with the Chicks' 2006 release Taking the Long Way. It debuted at No. 1 with sales of 526,000, and bounced back into the top 10 after earning five Grammys in February.
6. WOODY ALLEN MARRIES SOON-YI
Woody Allen films often feature unorthodox love stories, but he created the strangest one of all in his real life in 1992 when — during a bitter battle with longtime partner Mia Farrow over custody of their three children — the 56-year-old confirmed that he was in love with 21-year-old Soon-Yi Previn, Farrow's adopted daughter. (Farrow uncovered the relationship when she found nude photos Allen had taken of Previn in their apartment.) In 1997 Allen and Previn married; they now have two kids.
CAREER IMPACT: MINOR The director continues to release a movie each year — and has earned six more Oscar nominations. The thunderous ovation he received for his surprise 2002 Oscar appearance, meanwhile, was a fairly clear all-is-forgiven moment.
5. MICHAEL JACKSON DANGLES BABY
Michael Jackson and children. It's a tricky subject — ever since the King of Pop was first accused of molestation in 1993 (he settled out of court with the accuser in 1994). But until Nov. 19, 2002, the public never really had a clear picture of how the King of Pop related to kids; then they saw what he did to one of his own. While visiting Berlin, Jacko greeted fans waiting below his fourth-floor balcony by dangling his son, Prince Michael II (a.k.a. ''Blanket''), over the railing — as the baby wriggled and kicked under his one-arm grasp.
CAREER IMPACT: MAJOR The video of Jackson's shocking gaffe played endlessly around the world, offering another turn in the singer's downward spiral of molestation accusations (he faced more in 2005 but was acquitted) and plastic surgery as performance art.
4. HUGH GRANT'S DIVINE DRIVE-BY
Usually an actor's publicity tour for a new movie involves a round of talk-show appearances and magazine interviews. But just two weeks before the release of his 1995 comedy Nine Months, Hugh Grant put a new spin on PR when he was arrested in L.A. after police discovered him engaging in ''lewd conduct'' with prostitute Divine Brown. He was fined $1,180 and placed on two years of probation.
CAREER IMPACT: POSITIVE Thanks in part to his perfect apology on The Tonight Show (''I did a bad thing''), Nine Months ended up outgrossing his breakout hit Four Weddings and a Funeral with $69.7 million. The debacle actually seemed to enhance his charmingly rakish persona, which he put to good use later in Bridget Jones's Diary and About a Boy.
3. SINÉAD RIPS INTO POPE
Lorne Michaels and millions of Catholics were so not pleased when Sinéad O'Connor capped her 1992 SNL appearance by rending a photo of the Pope. Ripping up that picture on live TV was her dramatic way of making a statement about child abuse, she later explained, but by then outraged viewers were more interested in the singer's head on a platter.
CAREER IMPACT: MAJOR Radio stations banned her songs, fans destroyed her albums, she was fiercely booed at a Bob Dylan tribute two weeks later, and she never regained her platinum-selling status. In 2004 she took out a full-page ad in the Irish Examiner pleading with her country-folk to stop making fun of her.
2. MEL(T) DOWN
On the morning of July 28, 2006, Mel Gibson uttered 13 drunken words to L.A. County sheriff's deputy James Mee that would alter his career forever. ''F---ing Jews.... The Jews are responsible for all the wars in the world,'' said the actor-director, who also reportedly called a female officer ''sugar tits.'' (Gibson was arrested for DUI and pleaded no contest, receiving three years' probation and one year of mandated AA meetings.) He issued a statement July 29 apologizing for his ''despicable'' behavior and admitting to a battle with alcohol.
CAREER IMPACT: TBD Endeavor agent Ari Emanuel called for Hollywood to stop working with Gibson, and ABC canned a Holocaust-themed TV show he was producing. True, Gibson's next film, Apocalypto, made a solid $51 million, but studios aren't exactly rushing to cast him in, say, a sequel to What Women Want.
1. NIPPLEGATE
The Super Bowl is as American as apple pie. Flashing a bare breast on live TV during the Super Bowl, however, is not. That was quickly proven during the big game's Feb. 1, 2004, halftime show when Justin Timberlake tore off part of duet partner Janet Jackson's leather bodice, revealing a nipple-shield-adorned boob. With nearly 90 million people watching, many of them children, the incident became a flash point for family-values groups who had long argued that Hollywood was polluting kids' minds — and now they had proof. Timberlake apologized for the ''wardrobe malfunction,'' as did Jackson, who claimed the tearaway bra was ''an accident.'' But that did little to stop the ensuing tempest in a C-cup, which continued to make headlines throughout the year. The FCC issued CBS a $550,000 fine, politicians threatened bills that would ratchet up the punishment for future offensive broadcasts, and frightened radio stations began deleting naughty titles — e.g., Elton John's ''The Bitch Is Back'' — from their playlists.
CAREER IMPACT: MAJOR CBS would only allow Jackson and Timberlake to attend the Grammys if they apologized on the broadcast (she declined; he agreed). Jackson was also forced to withdraw as the lead of a planned ABC biopic on Lena Horne, and the Super Bowl controversy didn't help her 8th studio CD, Damita Jo (released weeks later), which sold just under a million. For reasons oft debated (racism? sexism? sheer popularity?), Timberlake emerged from the bra-haha unscathed.
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