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MTV VMAs: Justin Timberlake's Best and Worst Career Moments

UPDATED: The former boy bander will be honored with the Michael Jackson Video Vanguard Award on Sunday.

Justin Timberlake Tunnel Vision Screengrab - H 2013
Vimeo

Justin Timberlake is set to receive the prestigious Michael Jackson Video Vanguard Award at Sunday's VMAs (which, coincidentally, last went to his famed ex, Britney Spears, in 2011) and that has us feeling a bit nostalgic.

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Before JT was singing with Jay-Z, starring in hot films, wearing the five-timers club jacket on Saturday Night Live and shattering sales records, he was a fresh-faced, 11-year-old kid on Star Search. Later, he would go on to star on The Mickey Mouse Club circa the early 1990s with fellow future pop culture icons Spears, Christina Aguilera and Ryan Gosling.

Then 'N Sync was born and well, we all know what happened from there.

In the last year alone, Timberlake surprised fans with not one, but two new albums (The 20/20 Experience Part 2 is due out in September), starred opposite Ben Affleck in the Leonardo DiCaprio-produced Runner, Runner (out Sept. 27) and hit Cannes as a bona fide A-lister for the premiere of Inside Llewyn Davis, which went on to win the fest's Grand Prix Award. Lest we forget, he also got hitched to Jessica Biel in October of last year.

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But MTV is all about the music, right? And Sunday will no doubt highlight the superstar's music-related accomplishments -- and is even rumored to feature a reunion performance from 'N Sync.

Timberlake's longtime pal Jimmy Fallon will also be on hand Sunday to present the singer with his special Moonman.  

In honor of Mr. JT, The Hollywood Reporter looks back at a sampling of his best and worst moments over the years. But really, if we're being honest with ourselves, aren't they all the best?

"I Drive Myself Crazy" (1999)
This video… that hair… bad, bad bad. Is it so bad it's good? You be the judge.

"Bye Bye Bye" (2000)
Few dance moves have been burned into the memories of pop culture aficionados quite like "Bye Bye Bye." For what it's worth, the boys are expected to bring it back on Sunday's show.

 

Matching Denim (2001)
Add one to the harrowing halls of horrible fashion. The singer arrived with then-girlfriend Spears on his arm at the 2001 VMAs in matching Canadian formal wear. Worse: Justin paired his with a denim cowboy hat. We're certain this is one he'd love to forget, but we're having a tough time doing the same.

"Like I Love You" (2002)
The track was Justin's first offering as a solo artist and put him on the map as a legitimate, adult artist. The track was nominated for a Grammy Award and debuted at No. 11 on the Billboard Hot 100. (By the way, Justin debuted this song at the Video Music Awards.)

Nipplegate (2004)
While performing alongside Janet Jackson, things went awry and Justin accidentally (or not) ripped off a portion of his partner in crime's costume, exposing her breast to all of America. He went on to issue a scripted apology at the Grammy Awards (at the risk of being banned).

"SexyBack" (2006)
Mr. Timberlake, you have arrived.

Single Lady (2008)
Justin gave Beyonce a run for her money in a black leotard on SNL. That's all you need to know.

Justin Timberlake parodies Beyonce by LeNouvelObservateur
 

The Love Guru (2008)
Well, maybe this wasn't his best work... But he probably already knew that.

"Motherlover" (2011)
"Dick in a Box" might be the crowd pleaser, but "Motherlover" has so much to offer (read: Patricia Clarkson).

'Moron' (2011)
Timberlake made some waves when referencing his teenage (read: 'N Sync) years in a feature for Details, saying:  "There were many moments in my teenage years where I succumbed to, um, the weirdness of the group I was in. And in trying to conform -- we're marionettes! -- I ended up looking like a moron."
Hey, now…

The 20/20 Experience (2013)
Forget the surprise factor (OK, but seriously, how excited were you when that out-of-the-blue YouTube video hit?), but the album went on to sell 968,000 copies in its first week on the market.

Best Dressed (2013)
Thankfully, Justin be on his suit and tie s--t these days, making Vanity Fair's coveted Best Dressed list in a Tom Ford tux at the Grammy Awards.

"Mirrors" (2013)
This video, nominated for four Moonmen, including Video of the Year, is among his best offerings to date. Not only is the clip dedicated to Timberlake's real-life grandparents, but can we talk about his mirror shoes?!

What are you favorite Timberlake hits and misses? Hit the comments and let us know.

Email: Sophie.Schillaci@THR.com
Twitter: @SophieSchillaci