Justin & Cameron: It's Over
Timberlake and Diaz announce their breakup. "We have, in fact, ended our romantic relationship, and have done so mutually and as friends, with continued love and respect for one another," they say in a joint statement. In June, the exes reunite to promote Shrek the Third, in which they both star.
A New Leading Lady
Jessica Biel visits Timberlake in the U.K., where he is touring. They hole up in Manchester's five-star Lowery Hotel and take in a soccer match. She joins him on tour again in June, and the couple is photographed holding hands and sightseeing in Amsterdam and Stockholm. They were first linked at a Golden Globe afterparty in January and went snowboarding together at the Sundance Film Festival in Park City, Utah.
Scoring An Emmy, Two Grammys
Timberlake and Andy Samberg’s SNL music video, "D*** in a Box," wins a Creative Arts Emmy. The nomination alone for the risqué song, which describes gifting a male's genitals, surprises critics, fans and costar Samberg. "It's half cool, half surreal," Samberg tells PEOPLE. "I texted Justin but it's different for him he gets nominated for something every half hour." In 2008, Timberlake wins two Grammys for Best Male Pop Vocal Performance ("What Goes Around...Comes Around") and Best Dance Recording ("LoveStoned/I Think She Knows").
A Working Reunion
Timberlake reunites with ex Cameron Diaz on the Los Angeles set of their new film, Bad Teacher. In the romantic comedy, slated for a 2011 release, Diaz plays an irresponsible 7th grade teacher who pursues Timberlake's substitute teacher in the hopes of using his money for a breast augmentation. "They have a shared sense of humor," the film's director says. "It's easy for them to be funny together. You know where the jokes are."
Timberlake plays former Facebook president Sean Parker in The Social Network, a drama about the site's founder, Mark Zuckerberg. "I knew that it was in the two percentile of material that is just great," he says of the film, which opens at No. 1 and earns a Best Picture Oscar nod. "And then I heard David Fincher was going to be the director, and I peed in my pants a little bit."
Saying Bye Bye Bye
Only weeks after looking cozy together at an Oscar afterparty, Timberlake and Biel announce the end of their nearly four-year relationship. "The two remain friends and continue to hold the highest level of love and respect for each other," their reps say in a statement.
More Than 'Friends'?
Timberlake becomes a bonafide leading man in Friends with Benefits, a romantic comedy that pairs him with Mila Kunis. Though the film performs well at the box office, it's the chemistry between the actors that makes waves offscreen, prompting sources to insist that the two are just friends – without benefits.
Reunited & Engaged!
After spending five months apart, Timberlake reunites with Biel in Toronto before attending a friend's wedding together in Steamboat Springs, Colo. In the New Year, news of the couple's own wedding plans is leaked when a source tells PEOPLE Timberlake proposed to Biel while the duo vacationed in Montana.
Timberlake and Biel exchange vows in an intimate ceremony in southern Italy. "It's great to be married, the ceremony was beautiful and it was so special to be surrounded by our family and friends," the couple tells PEOPLE exclusively. Days before their nuptials, the duo kicked off their wedding celebration with a party featuring locally prepared delicacies and a beach bash complete with fireworks and live music.
The Seven-Year Itch
Following a seven-year absence from music, Timberlake debuts his new single, "Suit & Tie," and reveals that he will release an album, titled The 20/20 Experience, later this year. "Back in June of last year, I quietly started working on what is now, my next journey with the thing I love called MUSIC," he writes in an open letter to fans on his website. "The inspiration for this really came out of the blue and to be honest, I didn't expect anything out of it."
BIOGRAPHY (top to bottom): Jon Furniss/WireImage; Flynet; Gemma La Mana; Merrick Morton/Columbia Pictures; Kevin Mazur/WireImage; Jose Perez/Splash News Online; INF; Landov; Splash News Online