Shocking Moments When Good Singers Went Bad (And Sexy)

by Jordan Runtagh 1/23/2014

It’s gotta be hard if you’re a child star growing up in harsh glare of fame, and incredibly difficult to make the world take you seriously as you get older. As a result, some truly over-the-top antics are sometimes required in order for you to break free from the kid image and assert your independence as an adult! Read on to see some of the most aggressive “I’m not a child anymore” moments of all time. Look out, folks: They’re not that innocent.

9. Taylor Momsen Gets Pretty Reckless Onstage

She was little Cindy Lou Who, the priceless little child who brought holiday cheer to life in The Grinch Who Stole Christmas! She was the preppy (for a while, at least) Jenny Humphrey on Gossip Girl! Hell, she was even this little sweetie in the Shake ’n’ Bake commercial! But you can’t have the light without the dark, and we imagine all of this enforced cuteness as a kid caused her to store up a giant wad of rebellion, which came out in her rock ’n’ roll.

But Then:

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The eye-liner took over! “Music is where I can be me”, she said after she started recording with the band The Pretty Reckless in 2010. The group had some chart success, but the still-17-year-old grabbed more headlines for her risque (some would say age-inappopriate) behavior. She would make out with fans onstage, wore a shirt reading “I F–k For Satan”, filmed underage nude scenes for her music video, and gave masturbation advice…among other things. All in all, lots ’o’ aggressively (and intentionally) shocking behavior here, but we’ll give pride of place to when the still-underage singer went topless onstage. For us, that’s the moment she jumped the nudity shark.

8. Selena Gomez Goes On Spring Break

[Photo: PBS/Disney]

We Knew Her When:

Selena got her start on the PBS show Barney & Friends, so it doesn’t get more inoffensive than that. From there she moved on to the Disney Channel, charming the pants (no, not literally) off of kids and parents as Alex Russo on Wizards Of Waverly Place. Around this time she also charmed the pants (this time literally) off of fellow child-star Justin Bieber, creating an unstoppable union of wholesome teen cuteness…for a bit, at least.

Selena was seen as a sort of antidote to Miley Cyrus, Lindsay Lohan, Vanessa Hudgens, and other former-Disney starlets who were seen as getting too wild and crazy. Like many young actresses she tried to make the jump into music, and unlike many she actually succeeded, releasing three albums and scoring a few chart hits with her band The Scene, most notably “Love You Like A Love Song,” “Falling Down,” and “A Year Without Rain.” More than a few fans were bummed when she announced in January 2012 that she was putting her musical career on hold to focus on her acting. “This year is all about films and acting,” she said, but little did we know that we’d soon be seeing Selena in a whole new way.

But Then:

Yup, she shocked us all by appearing in Harmony Korine’s Spring Breakers, which features Selena getting up to laughably risky (and risque) shenanigans that we couldn’t have come up with in our wildest dreams! Considering that it’s stocked with former Disney star Vanessa Hudgens, as well as fellow-TV-good-girl Ashley Benson, we’re guessing that this was calculated casting designed to surprise. It’s all so campy and over-the-top that by the time Gomez resumed her (newly solo) music career last year with the more adult content of “Come and Get It”, the shock had warn off were definitely ready for it!

7. Justin Bieber Comes Of Age

We Knew Him When…

The story of Maple Jesus has already become modern myth. Videos of the 13-year old singing on YouTube were discovered by talent scout Scooter Braun in 2008, and the son of a young struggling single mom was launched into the pop music heavens. Simply put, the kid was ADORABLE, with his mop top hair and choirboy timbre. He became the prototypical child star, which has literally never ever ended badly, right?

But Then:

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We saw the signs when those pictures of him mackin’ it with bikini-clad ladyfriend Selena Gomez came to light in spring 2011. That had him up to a PG-13 rating. Then the rumors of him gettin’ down with Victoria’s Secret model Barbara Palvin, kicked things up a notch. Tattoos, fights with the paparazzi, Brazilian brothels, and even felonies and DUIs…we have to face the facts that our little Biebs has grown up! And in his new video for “All That Matters”, he wore his new adult ’tude on his sleeve, ditching the carefully choreographed dance moves for an intimate shirtless make-out session with a blonde model.

6. George Michael Wants Your Sex

We Knew Him When…

[Photo: CBS]

He was one half of Wham! (along side Other Guy), the ’80s pop due responsible for “Wake Me Up Before You Go Go,” without a doubt the most ludicrously joyful song ever made. Just look at the damn music video, consisting of the two guys dancing around in “Choose Life” t-shirts! Look at their smiles! You don’t get any less offensive. There are zero clouds on their horizons. Pretty much every song they ever made was insanely happy, even bummer ones like “Careless Whisper” and “Last Christmas” (the greatest Christmas song ever made). They are audio Prozac.

But Then:

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By 1987 Wham! had split and Michael went solo with his landmark disc, Faith, featuring lead single “I Want Your Sex.” Despite espousing the virtues of a monogamous relationship (how un-rock star), many people were shocked by this ode to…well, sex! The song was banned by radio stations across the globe, and many other disc jockey’s (including Top 40 guru Casey Kasem) refused to say its title. The racy video had gems like Michael writing “Explore Monogamy” on real-life partner Kathy Jeung’s back with lipstick. Poor George even recorded a prologue in which he insists “This song is not about casual sex,” but MTV still refused to play the clip before the watershed, and recently ranked it among the most controversial music videos of all time.

5. Miley Cyrus Can’t Be Tamed

We Knew Her When…

[Photo: Disney]

Yeah yeah, we all know the story here. Need we say more?

But Then:

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We’ve all seen enough Disney stars to know what was coming. South Park even predicted it years ago! Miley jumped from being a small screen hero for millions of little kids on Hannah Montana, to pursuing a serious Nashville music career. Her second album, 2008’s appropriately titled Breakout, hinted at the direction to come, and the 15-year-old courted further controversy that year with leaked bikini photos and a topless (save for a bed-sheet) Vanity Fair cover with taken by Annie Leibovitz.

By 2010 the 17-year-old was raising more eyebrows with her revealing concert attire, and her new single seemed to act as a direct answer to those critics who feared that she was leading her young Hannah Montana fans down an adult-themed path. “Can’t Be Tamed” and the accompanying video exploded in the spring of 2010, complete with steamy lyrics concerning freedom and self-exprression. It was hard to miss the metaphor, as the edgy and dark toned video had Miley trapped in a giant cage while gawking onlookers stared. After a series of sizzling dance movies, Miley The Exotic Songbird breaks out of her cage. Get the message? The wrecking ball, the twerking,the foam finger…it all started here.

4. Rihanna’s A Good Girl Gone Bad

We Knew Her When…

Riri was originally marketed as a reggae singer when she first came emerged on the scene in 2005 with her breezy debut album Music of the Sun. Steeped in the breezy Caribbean sound of her native Barbados, early singles like “Pon De Replay” and “SOS” performed admirably, but there wasn’t much to distinguish her from the pop crowd. It was as if she hadn’t found her individual voice and ran the risk of getting lost in what Slant Magazine called “a glut of teen R&B chanteuses” of the time. Even her style and fashion sense drew unfavorable comparisons to Beyonce.

But Then:

Her third album was aptly titled Good Girl Gone Bad, and signified a change in direction for the 20-year-old, moving her away from the dance-hall and reggae-influenced beats of old, and into harder-edged R&B. The disc featured darker cuts like the title track, “Hate That I Love You”, and “Breakin’ Dishes”, and got a hand from pro hitmakers like The-Dream and Timbaland, “I basically took the attitude of the bad girl and I really got rebellious and just did everything the way I wanted to do it—I didn’t want to listen to anybody,” she told The Star Phoenix at the time. “I just reinvented myself. I’m not the innocent Rihanna anymore. I’m taking a lot more risks and chances.”

The music video for the single “Umbrella” showcased Rihanna’s new style, including her trend-setting blunt bob and unique silver paint. The song (and album) went on to be a unbridled ’round-the-world smash. This incredible success perhaps encouraged Rihanna to continue embracing her inner bad-girl rebellious side, continuing on her next album Rated R, and evolving into the beloved controversy machine we know today. And we wouldn’t want her any other way!

**3. Janet Jackson’s janet. Album (1993)**

We Knew Her When…

[Photo: CBS/Getty Images]

She was the baby of the Jackson entertainment dynasty, appearing in their family variety show and bagging roles on classic sitcoms like Good Times, Diff’rent Strokes, A New Kind of Family and Fame. “No one ever asked me if I wanted to go into show business … it was expected,” she once said, and reluctantly began her singing career despite her desire to be a horse-racing jockey. She dropped her self-titled debut in 1982, and followed it up Dream Street in 1984. In 1985 she severed managerial contacts with her father, delivering Control the next year. Viewed as a great artistic leap forward, the record was still famously conservative in in tone, as illustrated by the sex abstinence anthem “Let’s Wait Awhile.”

But Then:

[Photo: Virgin]

The 27-year-old’s sexy side came to the forefront in 1993, with the release of janet, for which she wielded greater creative control than ever before. The sexual lyrics and themes of the music (with titles like “Throb” and “You Want This”) were viewed as a radical departure from her former fresh-faced image. “Sex has been an important part of me for several years,” she said in her infamous Rolling Stone cover story that borrowed the record’s artwork. “But it just hasn’t blossomed publicly until now. I’ve had to go through some changes and shed some old attitudes before feeling completely comfortable with my body. Listening to my new record, people intuitively understand the change in me.”

The record’s title (pronounced “Janet, period”) was her way of striking back at critics who claimed that she just coasted on her famous family name, asserting her artistic and sexual independence. The career-defining disc was a record-breaking smash, vaulting her into the superstar stratosphere, making her one of the most sought after women in pop, and solidifying her status as a major artist and sex symbol.

Britney Spears Does It Again At The 2000 VMAs

We Knew Her When…

[Photo: Walt Disney/Getty Images]

Britney Spears had been in the public eye since a young appearance on Star Search in 1991, and most notably in Disney’s The Mickey Mouse Club (along side Ryan Gosling, Justin Timberlake, and even Christina Aguilera). But she became lodged in popular consciousness forever while dancing by her locker in a (slightly altered) Catholic school uniform. 1998’s “…Baby One More Time” sewed the seeds of her legend, but at the time it made her a media darling. She famously announced that she would remain a virgin until marriage, presumably to her old friend and now flame, Justin Timberlake. They even had his ’n’ hers denim suits made up, y’all!

She weathered her fair share of controversies in 1999 and early 2000s, including a racy Rolling Stone cover and boob job rumors, but it was fairly standard issue for a teen pop star in the spotlight. By May 2000, Britney-Mania had reached a fever pitch with the release of her second album, Oops!…I Did It Again. A change was in the air…

But Then:

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Eager and anxious to begin ditching her bubble-gum sound and image, Britney used her appearance at the September 7th awards extravaganza to shake things up. After slinking her way through a cover the Rolling Stone’s “Satisfaction”, she tore off her MJ-esque suit to reveal a flesh colored body suit that scanned across TV cameras as nude, causing home audience (or at least 12-year-old us) to momentarily wonder if Brit had just ripped her clothes off on national television!

Obviously she definitely didn’t, but it was still a formative TV moment (for us, at least). She seamlessly shifted into “Oops!…I Did It Again,” dancing her heart out like she was born to do. As she purred the final “I’m not that innocent” to close the song, you knew she wasn’t kidding. Many saw it as the begins of her adult career as a more provocative entertainer, and certainly her tabloid headlines got much more salacious soon after. For all of the controversy and personal battles that followed, this performance remains one of her best.

1. Christina Aguilera Gets Stripped And “Dirrty”

We Knew Her When…

[Photo: Walt Disney/RCA]

Xtina is definitely not the only Disney alum on this list, and she even served on The Mickey Mouse Club alongside Britney Spears. At 17 she lent her voice to the song “Reflection” from the animated film Mulan, which earned the young singer a nomination for Best Song at the 1998 Golden Globes. Her 1999 self-titled debut album topped the charts with fun, catchy, inoffensive pop that didn’t get much darker than the inside of a genie’s bottle. Yes, “Genie in a Bottle” made her a teen music, going on to become the best-selling single of the year. Follow-up single “What A Girl Wants” was met with similar success, and also lent it’s title to an Amanda Bynes teen movie. In 2000 she released her own Christmas album, and even sang “The Christmas Song” at George W. Bush’s White House.

But Then:

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By 2002 she was “Dirrty”! Similar to Janet Jackson before her, Christina fired her old management and took greater creative control on new album, Stripped. The 21-year-old began co-writing “down and dirty” songs intended as a move away from her previous teen-pop sound. She penned the song “Miss Independent” during this period, and even though it went on to become a single for Kelly Clarkson, the message was clear: Christina was in charge!

“When you’re part of a pop phenomenon, you have so many opinions shoved down your throat,” she was quoted as telling USA Today at the time. “People try to tell you what you should do, how you should act, what you should wear, who you should be with. At the time things started happening for me, it was popular to be the squeaky-clean, cookie-cutter pop singer. But that role didn’t speak to me, because it’s so boring and superficial.”

Her look changed greatly in this period, as she dyed her familiar blonde dresses black, got several tattoos and piercings, and began posing nude on magazine covers. She dubbed this provacative new persona “Xtina”, and it caused quite a stir among fans used to her more conservative incarnation. To make the message even more obvious, the lead single was titled “Dirrty” and featured a vid which has regularly been ranked among the raunchiest of all time.

Jordan Runtagh

VH1 Music Editor + Seltzer Enthusiast

@jordanruntagh

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