Who: Three-time Emmy winning and 10-time Grammy winning actor and singer Justin Timberlake, 38, and four-time Golden Globe nominated actress Cameron Diaz, 46.
How They Met: Legend has it that Diaz and Timberlake’s first encounter was at the 2003 Kids Choice Awards when the Charlie’s Angels star presented the former NSYNC frontman with the prize for “Best Burp,” an award she herself had claimed just two years prior. It just goes to show, one burp really can change everything. Justin and Cameron owe four years of bliss (more or less) to a single, immaculate, bout of gas (probably).
Why We Loved Them: Burps! But physical comedy aside, Cam and J.T. really had each other’s backs. They handled a lot of weird Hollywood problems together: rabid paparazzi, tabloid libel, the pressure to wear matching jerseys to charity sporting events (see below). And through it all, they remained chummy enough to work together not once but twice post-split.
When They Peaked: The couple who SNLs together stays together (for around four years). J.T. elevated his lady love’s 2005 hosting gig when he made a cameo alongside Jimmy Fallon in a skit for the variety show’s recurring “Barry Gibb Talk Show” segment — Diaz played guest Nancy Pelosi (a latter day style icon) to Timberlake’s co-host Robin Gibb.
The Breakup: Though we can never truly know what went down between Cam and Justin, the Internet is rife with theories. The most sensationalist of the bunch suggests that the pair clashed over Scarlett Johansson’s involvement in Timberlake’s 2006 “What Goes Around … Comes Around” music video. At the time, Us Weekly reported that "Cameron was very jealous of Scarlett ... She could not believe he went behind her back to put her in the video," and that the jealousy was founded as Timberlake and Johansson "definitely got together after she did the video," again, that is according to Us Weekly at the time.
In response to the rumors, Johansson told Seventeen, “We live in a world today where if two people are single – and one’s a guy and one’s a girl and they’re both famous – you’re going to be linked with somebody. If it’s somebody one week, it’s going to be somebody else the next week. It’s either me or Jessica Biel.” Of course, Timberlake did end up dating (and marrying, and having a child with) Biel, but irony notwithstanding Johansson managed to hush the tabloid chatter.
Similarly, it’s rumored that Timberlake’s involvement with his future wife came between him and Diaz.
One week after he and Cam announced their separation in January 2007, complete with flowery PR terms like “love,” “respect,” and “friends,” the exes were seen engaging in a tense stand-off at Prince’s Golden Globes after-party. Diaz reportedly approached Timberlake while he was chatting with Biel, which according to a People story at the time, led to an “intense 40-minute face-off in a side room” that ended with the singer slamming his fist down on a cabinet.
In Timberlake’s 2018 memoir, the performer detailed his courtship with Biel, writing that though they’d flirted in the past, the night of the Golden Globes was what really solidified their bond.
“Then the Golden Globes came up, and that’s when we planned on seeing each other,” he wrote. “We were both still seeing other people, keeping ourselves safe from getting hurt, from really putting ourselves out there. It took a bit for both of us to admit to ourselves that we were really, really into each other.”
Though Justin and Cameron are both now married, and have been for years, neither was always so gung-ho when it came to commitment.
During a visit to the Ellen DeGeneres Show in 2006, the host asked Timberlake about the engagement rumors that long circled the pair. “I need to know, should I get a bridesmaid dress now or not?” she teased, to which Timberlake said, “Know what? Go ahead and reserve one. The only thing is, you'll have to stay the same size for the next 15 years."
Diaz’s thoughts on the topic seemed to be aligned. Two months after Timberlake’s Ellen appearance, the In Her Shoes star went on the show and told DeGeneres, “I’m a commitment-phobe. Don’t want to do it.”
The pair were forced to reunite just months post-breakup for the Shrek the Third press tour — but if there was any bad blood, you wouldn’t know it by looking at them.
Four years later, Justin and Cameron reunited again, and even shared a (very, very awkward) sex scene for raunchy 2011 comedy Bad Teacher.
Diaz gushed about her “frickin’ weird” ex, telling Us that Timberlake is “a genius comedian. . . he's clearly talented. He's so bizarre and hilarious.”
Where They Are Now:
Though Diaz has taken a step back from acting in recent years, her personal life has flourished. A “commitment-phobe” no longer, Cam wed Good Charlotte guitarist Benji Madden in 2015.
Timberlake released his fifth solo album, performed at the Super Bowl, and published a memoir last year, and of course married Jessica Biel, with whom he celebrated six years last October. The duo share a 3-year-old son, Silas.
A post shared by Justin Timberlake (@justintimberlake) on Dec 25, 2018 at 2:25pm PST