Since going solo, Justin Timberlake has worked extensively hard on creating the squeakiest clean image of himself possible. Despite the daily articles praising his music and funny moments with Jimmy Fallon, Justin's past is actually filled with questionable moments that paint a completely different picture from the one we are used to being fed in the media.
As a middle-aged woman who grew up mildly obsessed with the resident hottie of 90's pop music Justin Timberlake and his band of much less hot backup singers, aka N'sync, it actually pains me to write this article. If you are a JT lover like myself please go ahead and brace yourself for this forthcoming, disturbing information: our sexy-back babe Justin is kind of a shady dude.
I know what you are doing right now. You are throwing the stink eye directly at your computer screen, hating me for simply being the messenger of this deeply unsettling truth. Our golden boy is not Mr. Wonderful. He has made some truly questionable decisions in his adult years, many of which not even the most devout JT fan can get behind. It physically hurts to the one curly-haired crooner knocked off of his Golden pedestal.
Here are fifteen things Mr. Timberlake has done in recent history to get his fans talking and his middle-aged, obsessors bawling.
15 The 3-Day Fling With Mrs. Munn
Oh boy, more disappointing cheating rumors ahead folks! While we would like to believe that not a single one of these murmurings are true, there is something to be said about the timeless saying, "Where there is smoke, there is fire."
How Ms. Jessica Biel has tolerated and weathered years of these accusations about her now hubby and father to their son, I will never know. Then again she seems like a much more mellow lady compared to myself. Timberlake and Biel were still just boyfriend and girlfriend back in 2010 when he allegedly embarked on a three-day fling with actress Olivia Munn.
The rumor goes a little something like this: JT chased Munn, but she denied him because of his romance with Biel. Olivia is clearly no one's side-chick. JT insisted that he and Jess were through, even though this would have been news to Jessica, and that's when Munn said, "Eh, ok then. This is Justin Timberlake after all." Shortly after this story came out, Biel and JT did in fact break-up so either there is some truth to this one or she just couldn't deal with the constant rumor surrounding her man and his fidelity issues. We can barely cope either Jess.
14 Justin's Restaurant Lands Him In Hot Water
So after Justin conquered the music world before he even reached his 20's, he turned his attention to other ventures. Of course, he owns a record label, I mean everyone who is anyone in the biz has one to their name anyhow, but he also set his sights on the culinary scene.
I love JT just like the next 36-year-old woman, but why oh why do all entertainers firmly believe that because they are singers or actors, this talent will automatically transfer over to the restaurant biz? Justin opened a NYC eatery named after his southern roots. Southern Comfort seemed like a winning idea in theory, with Justin's name and face behind it and southern favs on the menu.
Too bad the concept wasn't the winning success that JT envisioned. According to Fame10.com, the establishment earned an embarrassing "B grade" compliments of a routine health inspection back in 2013.
The restaurant was docked a whopping 22 points for various violations and this wasn't even the first time the famous eatery found itself in hot water.
Southern Comfort was sued ten years ago, in 2008, by a busboy who cried foul when it came out legal wage payouts... Maybe don't quit that day job, Justin?
13 The Uproar On Twitter
Just a few short years ago Justin made heads spin when he took to Twitter to release a bit of a rant. The year was 2016 and racial tensions were high, clearly Justin wasn't paying too much attention to the climate of the country when he tweeted that he had been inspired by Jesse Williams inspirational speech.
Immediately backlash ensued and one journalist clapped back at him saying,"So does this mean you are going to stop appropriating our culture and music? Apologize to Janet too!", as reported by Nicki Swift. While Justin should be used to people occasionally hating on him, he tweeted right back saying, "Oh you sweet soul. The more you realize that we are the same, the more we can have a conversation. Bye."
Things snowballed really fast and a mere couple of hours later JT ended up issuing an apology and trying to smooth over the Twitter takedown. Perhaps Justin should steer clear of ranting and shooting off on social media channels considering the way he tends to be perceived. Trust me, it's hard not to fire back at someone shaming you on social media, as an entertainment writer I would know. The thing is it NEVER turns out the way you want it to. There is truly something to be said for taking the higher ground when it comes to matters such as this.
12 Lohan's Revelation... Real Or Fake?
Justin Timberlake has been linked with all sorts of famous women, both during his bachelor days and his days of being a taken man. We aren't shocked that he is constantly surrounded by rumors of late night trysts and steamy Hollywood hook-ups.
Just look at the guy. He is smoking hot and has a voice that can melt the ladies like a stick of butter. One such rumor that had fans frowning and shaking their heads though is the Lindsay Lohan hook-up rumor. Now before we go any further let's make something very clear.
This is kind of one of those he versus her hookups and LiLo is a little bit on the desperate side of fame these days, so it is completely feasible that she fabricated the entire encounter.
In 2009, Lohan accused Justin of being unfaithful to his then-girlfriend Jessica Biel...with her!
She claimed the two met up in NYC and spent some quality time together.
Lindsay later took to Twitter, posting cryptic messages such as, "Where's jb cheater?" and "Why do people cheat?" Word of caution JT, stay far away from Lindsay Lohan, regardless of whether or not you are hitting that or not.
11 'Friends With Benefits'
If JT was, in fact, making it a point to hook-up with women left, right and center while he was dating his now wife Jessica Biel, at least this rumor of him and lovely Mila Kunis is a step-up from his rumored fling with Lindsay Lohan.
Even though we hang our heads in shame at yet another Justin Timberlake dirty hook up, it's hard to not love Mila. She really is delish and it's understandable that Justin might have let his wandering eye get the best of him in this case. Mila and Justin spent a considerable amount of time together back in 2011 when they were filming the hilarious movie Friends with Benefits. According to Fame10, rumor has it perhaps life started imitating art because some scandalous pictures of JT were found on a hacked cell phone that reportedly belonged to Ms. Mila.
There was a photo of JT lying on a bed with his shirt off and women's undies on his head and one of Mila soaking in the tub. Considering the goofy personalities of these two the pics were probably all in good co-star bonding fun, but we aren't exactly sure Jessica Biel thought that same thing. Reps for both parties deny that any such exchange even occurred, but in Hollywood, who in the heck knows what's fact and what's fiction anyhow.
10 The Stain On Mr. Squeaky Clean
Compared to other incredibly famous and successful actors and musicians who are along the lines of Justin's caliber, JT seems fairly white bread. Sure he is sexy and he's got "moves like Jagger," but he isn't exactly a Jimi Hendrix or a Kurt Cobain. He has his blips on the radar but never seems to be engaging in anything too scandalous, especially considering his lines of work.
Allow me to burst everyone's idealistic bubble of a squeaky clean Justin. He is not nearly as straight and narrow as he is made out to be.
In an interview with MySpace regarding his first ever performance at SXSM Festival, Mr. Timberlake revealed that he has dabbled in the psychedelic world.
He explained that while this was indeed his first time at this particular festival, he had been to Coachella numerous times while on all sorts of mind-altering substances.
He went on to explain that while he had been to the famous grounds tons of time, he didn't always remember his stints there. One time, according to Fame10, he even stood in a field listening to Weezer while tripping out of his mind! While we aren't exactly shocked that a musician would spend time over on the dark side, this trippy reveal is a stark contrast to the Justin Timberlake of yesteryear N'Sync.
9 JT's Lyrics Causes Trouble
Songs, in general, will stir up emotions in humans regardless of whether or not they love them or hate them. JT's song Take Back the Night did just this with certain groups around the globe. So it seems that the non-profit organization that goes by the same name, and is aimed at ending non-consensual acts towards women, were none to thrilled about Justin's version of "taking back the night", nor were they tickled pink over him borrowing their group's name.
The racy words in JT's lyrics infuriated the organization and caused a bit of a stain on an otherwise smooth sailing Justin's lyrical track record. Timberlake ended up formally apologizing to both the group and the public saying that he had never heard of the organization and that this was all an innocent misunderstanding.
He let everybody know that his song had nothing to do with the group in any way, shape, or form and that he clearly supported the group's sentiments. Well, that's good I suppose. When you are as ginormous of an entertainer as JT is aren't there people on your staff who look into hiccups such as this though? It seems that there would be.
8 Did He Mock A Homeless Person?
At some point Jessica Biel decided to forgive Justin's maybe-cheating and agree to marry him in a 6 million dollar Italian wedding extravaganza. While the wedding sounded like the classiest affair in all the land, there was at least one awkward moment that took place across the pond and ended up getting leaked to the public, according to certain sources.
A video was reportedly shown at the wedding where droves of homeless people are taped congratulating the couple on tying the knot. People were enraged at the film saying that it poked fun at the less fortunate and was done in a mocking tone. JT went on the defense saying that it was silly and unsavory, but also claiming that he had zero knowledge nor involvement of the video prior to it being shown.
Justin let people know the video was done by good friends and lovely people who were in no way making fun of the homeless, but rather alluding to the fact that JT had few friends attend his nuptials.
He also claimed the video was never even shown at his wedding. We hope Justin doesn't make fun of homeless folk, but the guy does have an out of the box sense of humor and is human after all.
7 His Break-Up Anthem Was Heard Around The World
Who can forget Justin's epic break up anthem Cry Me a River? It's one of those songs that is forever ingrained in our brains for one reason or another. Justin's first love was none other than the infamous Britney Spears. The two teen pop stars were the Ken and Barbie of the entertainment world, accompanying one another to various awards shows in their matching denim ensembles and setting the bar way to high for achieving couple's goals. Then the Royal couple of teen pop music hit the skids.
The pair went their separate ways and BAM! Cry Me a River hit the airwaves. According to producer Timberland, Justin penned the song following a not so pleasant conversation with Brit Brit, although the singer has never come forth and confirmed such rumors. Adding a bit more fuel to the messy fire, according to Fame10, Justin allegedly made a statement at a 2013 Superbowl party that went along the lines of, "Sometimes in life you think you've found the one. But then one day you find out that she is just some b." Was this statement directed at his once love Britney? He says no of course but we think that perhaps JT will never quite get over the Pop Princess.
6 The Royal Diss
So it seems that JT has a bit of a history when it comes to throwing shade at iconic and now deceased entertainer Prince.
At the 2007 Golden Globes the singer accepted an award on Prince's behalf by squatting down and assuming a comical, and probably offensive, short stature, as reported by NickiSwift.
The year prior to this there was some dialogue between the musical men about whether "sexy was actually back" or had it not left in the first place? So a decade after the beefing started JT plays a tribute show to Prince at the 2018 Superbowl in Prince's hometown. Prince fans were not thrilled and even JT fans cringed at his less than best performance.
JT wanted to include a hologram of the late entertainer in his show, but people close to the late star were adamant that Prince would have rolled in his grave over this idea. Prince apparently thought holograms were weird and demonic. Maybe JT was unaware of the deceased singer's feeling on the show gimmicks, but also maybe this was his last hoorah at throwing shade Prince's way. If that's the case it's pretty shameful and sad considering the guy was already six feet under when Superbowl tribute plans started.
5 He Sold Britney Spears Out To Barbra Walters
To say that Justin struggled after his break up with Pop star Britney Spears would probably be a gross understatement. He not only penned and released Cry Me a River directly following their split, but he also created a music video that had some undeniable Brit-Brit parallels.
His shade-throwing frenzy didn't stop there though. He also gave a candid and exposing interview to Barbara Walters following their fizzled out romance and released all sorts of juicy factoids regarding their now-dead relationship.
We can't believe our JT was such a kiss-and-teller. Britney had already told the press that she planned on remaining chaste until marriage, but JT let the world know that they had in fact been intimate. Clearly he was a boyfriend scorned. He also brought up their initmacy in a 2009 Saturday Night Live Sketch. Britney was furious. She told the press that they did the deed years into their romance and she truly though he was the one. Britney went on to express her disdain for Justin in regards to him selling their private secrets to the press and exposing parts of her that she clearly didn't want exposed.
4 He Might Have Stole A Song
If there is one thing Justin seems to pretty much always get right, it's his music. He has been performing and writing songs for decades and always manages to remain sexy, talented and relevant. This is one thing that makes him stand out in a sea of singers, so when we hear that he might be a bit of a song stealer we can't help but cringe. In 2016 Justin was accused of stealing three songs from different writers and this resulted in three lawsuits.
The year 2016 really wasn't JT's year if you think about it. Two members of the 70's band Sly claimed that Justin's Suit and Tie was a rip off of their song Sho' Nuf'. They sued the singer over the similarities and lack of royalties and credit. Then Damn Girl was apparently not the "product of independent creation." The claim was that it was taken from the 1962 song A New Day.
Lastly Cirque de Soleil took at crack at Justin claiming that his Don't Hold the Wall was ripped off of their song, Steal Dreams.
Justin this song stealing of yours makes us very sad. We can't hold you in the highest musical esteem here if you know that you are less of a musical genius and more of a musical thief! Tell us that none of this is true and these people are simply jealous so that we can continue on worshiping you.
3 Haft-Time Hootenanny
It was the nip slip seen round the world. Let me take you back to the year 2004 for just a second. We all sat on our couches, stuffed to the brim with beer and nachos, as we watched JT and Janet Jackson tear up the Superbowl halftime show singing JT's super hit "Rock your Body."
Then it happened. We all suddenly got very close with Ms. Jackson and her body parts. Justin intentionally ripped open a flap on Janet's outfit exposing one of her absolutely perfect tatas, according to Fame10. When JT belted out the lyrics, "Gonna have you naked by the end of this song, he clearly really meant it." Nipplegate was all anyone could talk about for months on end. There were haters, there were lovers and regardless of what side of the scandal you fell on, you were talking about it.
Janet herself cried wardrobe malfunction over the incident saying that although the move was planned it wasn't intended to be so scandalous. She swore that during the infamous rip her lacy under trappings came loose exposing her bare skin. No one was really buying that though. When all was said and done Justin's career suffered not at all while Janet was pretty much blacklisted in the entertainment industry for good. Her music was pulled from the American radio stations for the Superbowl nude-move and Janet's career never made a comeback. Boo to that! Janet is the bomb.
2 No longer In-Sync With N'Sync
Justin has been making music on his own for so long now it's almost unfathomable to think that there once was a time where he was completely united and synonymous with these guys. His fellow members of the mega boy band N'Sync never quite made it on their own as solo entertainers like JT did. It must be hard to forever be in the shadows of the oh so glorious one.
Even though Justin was the obvious star in the group, he has pretty much shunned and dissed the dudes who helped him makes his first millions and aided him in getting his name in lights.
According to Nicki Swift, the guys who were pretty much like brothers at one point in JT's life weren't even invited to his wedding to Jessica Biel!
It's okay fellas, we weren't invited either and we are still burning a bit over that too. In 2013 another diss hit the other band members when they were invited to perform with Justin for his Video Vanguard celebration at the 2013 MTV Music Video Awards. While the guys did pop out of the stage for a few minutes of bopping around they weren't there for long. Their super brief cameo was upsetting to the guys, even though truly they should maybe be thanking Justin for ending the embarrassment when he did. The dudes were a little out of practice.
1 The Questionable Cornrows
The single most questionable thing that Justin has ever done to make all of us question our love for him though is when he came out rocking cornrows and John Lennon sunglasses. We all had to sit down and truly consider our devotion to the guy when this image came about. Our handsome crooner looked like a horrifying wreck. Now we all made some poor fashion choices back in the early nineties, no one is exempt from this, but please Justin why oh why did you make us love you through this phase?
This hairstyle didn't last for very long, thank goodness, and when it finally disappeared for good we all breathed a sigh of relief. Justin brought sexy back and we could all publicly proclaim our admiration for the man again without the sting of cornrow shame. Clearly Justin truly is human, although we have actually questioned this theory a time or two. he makes mistakes just like the rest of us, he jests in poor taste and he seems to have a bit of a wandering eye. Our Golden boy can do wrong..but we still love him and we will never, ever fully say Bye, Bye Bye.