Justin Timberlake's 10 Hottest Hook-Ups

Justin Timberlake is the exception to the boy band curse. The former 'N SYNC frontman, who turned 31 years old this week, has not only escaped exile to the island of cheesy late '90s pop stars, where his 98 Degrees and Backstreet Boys bros will forever reside, but his taste in women is admirable.

Thanks to excellent management, some major movie roles, and his Emmy-winning "Dick in a Box" skit, Timberlake reached a level of solo stardom that puts him on par with some of Hollywood's most desired leading men. Thus, good enough for the town's leading ladies. Check out this list of Justin Timberlake's Hottest Hook-Ups and we promise you'll forgive him for bleached tips and bubble vests.

When: May 2011
In random celebrity dating news, Justin and Ashley allegedly rebounded with each other after breaking up with their long-time partners, he with Jessica Biel and she with Justin Bartha. According to Us Weekly, the two former child stars were reportedly spotted together at Greenwich Hotel, a Saturday Night Live after party and polo mouth outside the city. When asked about their relationship, Justin's rep denied their intimate involvement.

Smash Probability: Olsen probably redefined the phrase "New York minute" for him.

When: Mid 2002
Dewan seems to have a penchant for falling for her dance partner. Mrs. Channing Tatum of Step Up fame reportedly began dating Timberlake right after his split with Britney Spears in 2002, while she was still one of his background dancers. The two inspired tabloid stories after being seen leaving a Los Angeles nightclub together.

Smash Probability: The pair likely practiced the horizontal tango together.

When: September 2010 - October 2010
According to Us Weekly, Timberlake began cheating on Jessica Biel with Olivia Munn after meeting her at a MySpace event. Timberlake allegedly lied to Munn about the existence of his relationship to Biel, which made Munn more eager to take him back to her hotel.

Smash Probability: Given the mag's source for the story, a.k.a. "the insider," also alleged they had "amazing sex" that night, this hook up is probably the product of someone's wild imagination.

When: Early 1999 - March 2002
Justin Timberlake and Britney Spears were like the Brangelina of teeny boppers. The two had a fairy tale story prime for the pages Tiger Beat, the pair met during their stint on The Mickey Mouse Club and reconnected when they started going on tour together in 1999. Unfortunately, the pair fell apart after rumors of Spears' infidelity with then-choreographer, Wade Robson. The rumor was fueled by Timberlake's single and music video, "Cry Me A River," in which two people resembling Spears and Robson are featured having an affair.

Smash Probability: Although their relationship wasn't a front, Justin later admitted their respective virginity was.

When: April 2003 - January 2007
Despite her cougar status of being nine years older than him, Diaz and Timberlake's very public relationship lasted for almost four years before the two announced their split after facing increasing pressure from the tabloids. One minute they were allegedly cheating on each other, the next they were engaged.

Smash Probability: Bad Teacher wouldn't have been so awkward to watch if they weren't famous exes.

When: September 2002 - October 2002, January 2007
Before actress Alyssa Milano got married and had a baby, she seemed to be Timberlake's favorite shoulder to cry on. The two dated back in 2002, shortly after he split from Britney Spears. They would be seen doing everything from clubbing to playing golf together. In January of 2007, after announcing his split with Cameron Diaz, Timberlake was linked to Alyssa Milano again. This time, witnesses in Vegas saw them dancing together at Jet nightclub.

Smash Probability: It's safe to say Alyssa Milano showed him who's boss.

When: April 2011
After separating from her husband of eight years, Olivia Wilde, then on the rise to A-list status, was linked to many of the Hollywood men she was even momentarily seen with, including Bradley Cooper and Justin Timberlake. Wilde and Timberlake, who played mother and son in the film In Time, were allegedly caught canoodling at The Roxy in Los Angeles one spring night.

Smash Probability: We'd say Timberlake's oedipus complex likely kicked in for at least an evening.

When: January 2007 - March 2011, July 2011- Present
While Jessica Biel and Justin Timberlake have yet to personally confirm their reported engagement, one credible source has seemed to have already done that for them. Timberlake's grandma, Sadie Bomar, recently told Gossip Cop that her grandson called her last Christmas day to share the news. Timberlake and Biel have been dating on and off for about five years, with rumors of infidelity and potential rebounds previously marring their relationship.

Smash Probability: We're willing to believe grandma over Biel's lack of engagement ring at the 2012 Golden Globe Awards.

When: January 2007, September 2011
Rumors about Timberlake and Johansson began circulating when Johansson was cited as the alleged reason Timberlake and Diaz broke up. Reportedly, Diaz held a grudge against Johansson, who was cast in Timberlake's video for "What Goes Around, Comes Around," starred in Lost In Translation, in which Anna Faris' ditzy character was supposedly based on Diaz, and dated Diaz's ex Jared Leto. Johansson and Timberlake, who was still dating Jessica Biel at the time, also reportedly reconnected in September 2011 in New York, where they were spotted clubbing together.

Smash Probability: Anyone who saw Timberlake's video for 'What Goes Around, Comes Around" would assume the two superstars worked on their chemistry off-screen.

When: June 2011 - August 2011
The Friends with Benefits co-stars allegedly had their own play dates off-screen last summer while promoting their new rom-com. Despite their reps denying their relationship, it seems that no one is willing to believe the two are platonic, no thanks to them groping each other at the 2011 MTV Movie Awards.

Smash Probability: Their comfortableness with each other pretty much invalidates any statement that they were never physically intimate.