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.

Former Playboy model Zoe Gregory claims she once hooked up with Justin Timberlake while the “SexyBack” crooner was dating Cameron Diaz in the early aughts. The blond bombshell, now 49 ...

and we both got our kit off — down to his shorts — and we ended up fooling around.” Gregory alleged she and Timberlake did “not have sex” but claimed they fondled and “made out.” ...

However, Gregory claimed that after she teased Timberlake that Diaz was “not with [him] now,” the pair allegedly hooked up in Hugh Hefner’s indoor pool at the Playboy Mansion in Los Angeles.

LONDON – JUNE 11: Actors Justin Timberlake and Cameron Diaz arrive at the UK film premiere of ‘Shrek The Third’ at the Odeon, Leicester Square on June 11, 2007 in London, England.

This could have been one of the most iconic couples (and weddings) in Hollywood. However, numerous incidents, the harassment of the media, and many up and downs led this power couple to break up.

Matthew Perry reflected on once going on a date with Cameron Diaz ... he and Diaz were set up shortly after her 2007 split from Justin Timberlake. Perry, 53, writes in his book that he remembers ...

Rolling Stone founder Jann Wenner has seemingly dissed Cameron Diaz in his ... of the actress kissing Justin Timberlake on a surfboard. FameFlynet / BACKGRID Diaz, 50, and the “NSYNC” alum ...

Here's the complete timeline of their relationship thus far. Shortly after his break up with Cameron Diaz, Justin Timberlake and Jessica Biel are seen snowboarding together with a group of friends ...

Justin Timberlake and Jessica Biel are in “7th ... and his subsequent relationships with Emma Bunton and Cameron Diaz — Timberlake began dating Biel. The duo got engaged in 2011.

Justin Timberlake, and Alex Rodriguez. She married Good Charlotte guitarist Benji Madden in 2015, and they have two children together. Cameron Diaz’s net worth is estimated to be around $140 ...