Before he made his Saturday Night Live debut, it wasn't entirely clear if the former Mouseketeer actually had a sense of humour. But the festive leer of Dick in a Box left no doubt in our minds. Viewed more than 35 million times on YouTube, the song became a regular request on radio and went on to win an Emmy Award for Outstanding Original Music and Lyrics. Three years later, Andy Samberg and JT reprised their roles for the sequel, Mother Lover.
Unlike his music, JT's acting career hasn't featured a consistent string of hits. But The Social Network was a major breakthrough for the performer, playing Napster founder Sean Parker. The film earned JT widespread critical acclaim and was nominated for eight Oscars, including best film. A career highlight that was mildly tarnished a few weeks later, when Yogi Bear was released featuring JT as Boo-Boo.
Friends With Benefits (2011)
Justin proved he could be funny and charming when he took on the lead in this romcom, starring opposite Mila Kunis. Curiously, it was released just months after the near-identical premise, No Strings Attached, which was the name of NSYNC's best-selling album. He acquitted himself admirably and proved his acting strength really does lie in comedy.
The Love Guru (2008)
Justin Timberlake in a scene from The Love Guru.
It's the best of the bad (and there are more than a few contenders... ) God knows what Justin was thinking when he signed on to this Mike Myers' trainwreck of a film but we're sure he still rues the day. Timberlake played the nemesis of the piece, famous for his large appendage. The only thing worse than the film was watching JT squirm through all the publicity interviews.
History of Rap (2010)
It began in 2010 with Rapper's Delight and continues to this day. Every time JT stopped by Late Night with Jimmy Fallon (and now The Tonight Show), the pair bust out another instalment of their hip-hop mash-up, The History of Rap. From Kriss Kross to Jay-Z and everything in between, this ongoing series showcases the best of JT - humour, slick dance moves and insane musicality.
