Cameron Diaz and Justin Timberlake: Timing Was off for Marriage

Who

Four-time Emmy-winning and 10-time Grammy-winning actor and singer Justin Timberlake and four-time Golden Globe-nominated actress Cameron Diaz. She was 34 when they met, while Timberlake was 25.

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. They 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, Diaz and Timberlake really had each other's backs. They handled a lot of weird Hollywood problems together: rabid paparazzi, tabloid libel, and 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). Timberlake 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 Diaz and Timberlake, 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 2 children 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 People, 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 Diaz and Timberlake are both now married and have been for years, neither was always eager 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, they reunited again and even shared a (very, very awkward) sex scene for the 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 (we haven't seen her on the big screen since 2014), her personal life has flourished. A "commitment-phobe" no longer, she wed Good Charlotte guitarist Benji Madden in 2015. Four years later they welcomed a daughter via surrogate, Raddix.

Now, Diaz is slated to un-retire, and star in a Netflix film alongside Jamie Foxx called Back to Action.

As for Timberlake, his fifth solo album was released in 2018, which was the same year he performed at the Super Bowl and published a memoir. He has two upcoming movies, including Reptile and Trolls 3. And of course, he's still married to Jessica Biel, with whom he celebrated 10 years of marriage in October 2022. The duo shares 2 sons — Silas who was born in 2015 and Phineas in 2020.

#TBT: Check in every Thursday as we throw it back to some of our favorite celebrity couples of all time.