Contact Us

10 Not-So-Cool Justin Timberlake Moments

Justin Timberlake
David Becker, Getty Images

Justin Timberlake‘s ’The 20/20 Experience’ sold almost 1 million copies in its first week of release. His prior album — ‘Future Sex/Love Sounds’ — is considered one of the decade’s greatest albums. The singer has also won two Emmys for Outstanding Guest Actor in a Comedy Series. He also sang in ‘D— in a Box.’

“Timberlake does a lot of things well” is the gist of what we’re trying to say here. Ever since he became a part of ‘The New Mickey Mouse Club’ when he was 12, the entertainer has been scoring home runs whenever the spotlight shines on him. It doesn’t matter if it’s when he’s making boy band hits, acting in major film releases (see: ‘The Social Network’) or performing live, it always feels like Timberlake succeeds.

We say “feels like” because he is a human being after all and closer inspection into his career and personal life shows he doesn’t necessarily always come out on top. He’s been able to avoid extreme, potentially career-ending fails, but there’s still a couple of blips here and there that are still pretty hard to ignore, no matter how big he gets. TheDrop.fm recollects a few in 10 Not-So-Cool Justin Timberlake Moments.


Wearing Cornrows

 
 
 
Getty Images
Getty Images

It's these Stevie Wonder-esque braids that had people picking Lance Bass or J.C. Chasez as the potential breakout solo stars after 'N Sync disbanded. Yes, Timberlake had the bleached hair and rocked the Jheri curls, but that’s all right. The man helped make ‘Bye Bye Bye’ so a lot of this was forgivable. JT's going to need to couple more millions for this braided tragedy to fall by the wayside.

Throwing Janet Jackson Under the Bus After Super Bowl Incident

 
 
 
Donald Miralle, Getty Images
Donald Miralle, Getty Images

A lot of people didn’t know “wardrobe malfunction” could be used as a term before the infamous incident at the 2004 Super Bowl. Justin Timberlake was performing ‘Rock Your Body’ at the halftime show with Janet Jackson onstage, and to close out the performance, he tried to tear away her bustier. Timberlake’s “I'ma have you naked by the end of this song” became too literal when he ended up exposing Jackson’s right breast (with a nipple shield, but still, kids were watching). The FCC wasn’t pleased, CBS was angry at the $550,000 it got hit with and the New England Patriots must’ve been upset because too few ended up caring about them winning the Super Bowl.

What makes this a JT fail? Timberlake issued an apology and quietly sidestepped from the controversy, while Jackson and her nipple took the brunt of the criticism. Not exactly a ride-or-die move by the former boy band singer.

Locking Himself in a Room Listening to Queen

 
 
 
ShowBizIreland, Getty Images
ShowBizIreland, Getty Images

With that guitar solo and Freddie Mercury showing once again he’s one of the greatest of all time, very few can argue against ‘Bohemian Rhapsody’’s epicness. But is the grandeur so weighty that it forced us to abandon our social lives and lock ourselves in our room upon a first listen? Of course not, because that’s ridiculous … unless you’re Timberlake.

"I remember I listened to 'Bohemian Rhapsody,' by Queen, over and over,” Timberlake said in an interview with Rolling Stone. “I locked myself in my room and turned off the lights and listened to it for two days straight. I'd only come out for food or water. I wanted to dissect every part of it.”

That’s weird activity, but he became one of the greatest pop artists of this generation. The question now is why aren’t we locking ourselves away for two days in our bedrooms to listen to Queen?

Performing on 'Star Search'

 
 
 

A lot of us have those very embarrassing childhood photos or VHS moments that someone has that we’d just wish would go away. That’s not so simple for Timberlake since he later became a star. He’ll just have to deal with the fact that 11-year-old “Justin Randall” performing a country hit on ‘Star Search’ will be easily accessible to watch forever. Or as long as the Internet exists.

Realizing Tennman Records Isn't Doing Too Well

 
 
 
Getty Images
Getty Images

Justin Timberlake started Tennman Records in 2007, around the time he solidified his place as a new king of pop. Since then, the singer has signed three artists ranging from country to pop. Also, since then, none of those artists have made so much as a dent on mainstream consciousness. Timberlake is still the most -- and only -- recognizable name on the label.

Being Introduced by Cameron Diaz on 'SNL' After They Split

 
 
 
Lisa Blumenfeld, Getty Images
Lisa Blumenfeld, Getty Images

Timberlake’s romantic conquests include Britney Spears, Mila Kunis and Cameron Diaz. The latter one caused a lowkey awkward undertone when she introduced Timberlake on 'Saturday Night Live' in 2006. They’d just broken up, so the gesture must’ve caused quite a bit of side glances and giggles from the viewers at home. Cameron Diaz and Justin Timberlake would later collaborate on the film 'Bad Teacher.'

Appearing on 'Punk'd'

 
 
 

The 'Mirrors' crooner has been in show business his whole life, so it’s understandable he’d be a little bit thrown off at the idea of being homeless. But when Ashton Kutcher 'Punk’d' him under the facade of seizing government property, it’s hard to predict the near complete emotional breakdown JT has. There was no sense of cool here, from Timberlake calling his mom to whining as the “workers” break down his guitar. Chances are he would’ve been balling if Kutcher only prolonged his arrival a little bit more.

Crying Himself to Sleep After Britney Spears Breakup

 
 
 
Kevin Winter, Getty Images
Kevin Winter, Getty Images

As cool as Timberlake is, you may get the image of him just slicking back his hair and doing the sidestep shimmy through a door if he ever gets news of a breakup. He wasn’t always the ‘Suit & Tie’ guy we know today though. Back in the 2000s, Timberlake was a singer with some fragile emotions, which got broken by his childhood sweetheart, Britney Spears. He admitted to shedding many tears after the couple parted ways. We doubt Drake ever had it this bad.

Getting Bashed by the O’Jays

 
 
 
Jim Ross, Getty Images
Jim Ross, Getty Images

By 2005, JT had sold millions of albums as part of ‘N Sync, had a successful solo debut and made the classic ‘Cry Me a River.’ He still wasn’t quite impressive enough to induct the O’Jays into the Rock and Roll Hall of Fame, according to the O’Jays themselves. The legendary group reportedly vehemently protested Timberlake doing the honors. "We protested, kicked and stomped,” said band member Eddie Levert. “But it is out of our control." We wonder if their opinions changed, especially after Timberlake sold nearly a million copies in a week of ‘The 20/20 Experience.’

Collaborating with Nelly on 'Work It'

 
 
 

Even though Nelly has a lot of hits, his cross-genre collaboration record leaves a lot to be desired. His 2003 single featuring Timberlake provides a case in point. The two produced a track that's so sleazy and grimy, listeners may feel the need to wash their hands upon a first listen. There probably won't be a second listen either. Nelly later one-upped himself with 'Over and Over,' the grating collaboration with country star Tim McGraw.

Best of the Web

More From Around the Web

Leave a Comment

It appears that you already have an account created within our VIP network of sites on . To keep your points and personal information safe, we need to verify that it's really you. To activate your account, please confirm your password. When you have confirmed your password, you will be able to log in through Facebook on both sites.

Forgot your password?

It appears that you already have an account on this site associated with . To connect your existing account with your Facebook account, just click on the account activation button below. You will maintain your existing profile and VIP program points. After you do this, you will be able to always log in to http://thedrop.fm using your Facebook account.

Please fill out the information below to help us provide you a better experience.

Register on TheDrop.fm quickly by logging in with your Facebook account. It's just as secure, and no password to remember!

Not a Member? Sign Up Here.

Register on TheDrop.fm quickly by logging in with your Facebook account. It's just as secure, and no password to remember!