MTV VMAs: Justin Timberlake's Best and Worst Career Moments
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 November), 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.)