Early in 1999, he began what eventually became a high-profile celebrity relationship with fellow pop singer Britney Spears, with whom Justin Timberlake had worked on the New Mickey Mouse Club. This ended abruptly in March 2002, amidst tabloid press speculation on Spears' infidelity with choreographer Wade Robson, a mutual friend of Spears and Timberlake. Lynn Harless says as a mother she too was devastated regarding the break-up, but to this day speaks warmly of Spears, "Britney grew up on my living room floor. I still love her to death. They (Justin and Britney) were together 10 or 11 years and had, from day one, instant chemistry between them. She's a sweet girl. I just hate what she's going through now." The breakup influenced the lyrics and theme of Timberlake's hit "Cry Me A River", one of the most popular singles from Justified.
Post-Spears, Justin Timberlake has generally refused to discuss his personal life with the media, as a result of which his relationships have been the subject of much speculation in the tabloid and celebrity press. Justin Timberlake was involved with singer-actress Stacy Ferguson prior to 2001. He was romantically linked with actress-dancer Jenna Dewan (in mid-2002) and actress-singer Alyssa Milano (between September and October 2002). He began dating actress Cameron Diaz soon after they met at the Nickelodeon Kids' Choice Awards in April 2003. Regular rumours of break-ups reported in the tabloid press were either ignored or occasionally denied. On the December 16, 2006 episode of Saturday Night Live, Cameron Diaz introduced Justin Timberlake as the night's musical guest, and the couple officially split shortly afterwards. After the tabloid press alleged an affair between Justin Timberlake and Scarlett Johansson, with whom Justin Timberlake had shot the video for his single "What Goes Around.../...Comes Around Interlude", Diaz and Timberlake issued a joint statement on January 11, 2007:
Lovestoned Justin Timberlake Life karl wolf
| “ | It has always been our preference not to comment on the status of our relationship, but, out of respect for the time we've spent together, we feel compelled to do so now, in light of recent speculation and the number of inaccurate stories that are being reported by the media. We have, in fact, ended our romantic relationship and have done so mutually and as friends, with continued love and respect for one another. | ” |
Later in January 2007 Timberlake was linked to Jessica Biel when pictures surfaced of the two snowboarding in Park City, Utah during the Sundance Film Festival. On May 12, 2007 romantic pictures of Timberlake and Biel on multiple dates were published. In the August 9–15, 2008 edition of Heat magazine, when Timberlake was asked to describe his perfect woman, he replied "About 5ft.7in.-5ft.8in., nice butt, Midwestern American, kind-of-German last name, green eyes, big pouty lips, fair skin, ahhh....sinewy bod..." However, during an appearance on the The Tonight Show With Jay Leno on June 11, 2008 when Jay Leno questioned him about anything related to rumors of engagement and pregnancy, Timberlake jokingly responded that he "is engaging in a conversation with Leno" and "everybody in general can get pregnant."
Timberlake was given Sexiest Man titles by Teen People and Cosmopolitan magazines. On February 17, 2009, Timberlake was named the "Most Stylish Man in America" by GQ magazine.
