Who: Oscar-winning actor Matthew McConaughey, 48, and Oscar-winning actress Penelope Cruz, 44.
How they met: The actors initially got together on the Morocco set of 2005 action comedy Sahara.
Why we loved them: In retrospect, Penelope and Matthew were two of America’s most underrated actors when they began dating. Though Cruz was a major star abroad, she’d been relegated to sex-symbol status in America — similarly, McConaughey was on a rom-com love interest streak until around 2011.
The breakup: Though the duo’s reps attributed their 2006 split to “busy work schedules,” there are rumors that Matthew was still with Penelope when he met his future wife Camila Alves. According to Matthew McConaughey: The Biography, the Mud star was dating Cruz when he first saw Alves at the Hyde Lounge in West Hollywood. "My eye went up and I remember what came out of my mouth. I didn’t say ‘Who is that?’ I went, ‘What is that?’ As l was trying to get her attention across the room, I went in my head, ‘This is not the kind of woman you call over across the room, McConaughey. Get your ass out of your chair and go get her.’ Which I did,” McConaughey told People of his first time seeing Alves. “We went on our first date three nights later and I knew then I’ve been wanting to go on a date with her for the last nine years and not with anybody else.” Matthew also clarified that he was “happily single” at the time, so the biography’s assertion should be taken with a hefty grain of salt.
Where they are now:
Both Matthew and Penelope have thrived romantically and professionally since their 2006 split.
Cruz earned her first Academy Award nomination in early 2007 for her work on Volver, followed by her first win in 2009, and a third nomination in 2010. The actress also earned her first Emmy nomination this year for her performance as Donatella Versace in Ryan Murphy’s American Crime Story anthology series.
In 2007, she began dating fellow Spanish actor Javier Bardem (whom she’d been working alongside since 1992!). The gorgeous couple wed in 2010 and has since welcomed two children together: Leo, 7, and Luna Encinas Cruz, 5. Bardem and Cruz’s latest project, Everybody Knows, just celebrated its premiere at the Toronto International Film Festival.
McConaughey steadily added a series of more serious performances to his oeuvre before landing his first Oscar nomination (and win!) for 2013 drama Dallas Buyers Club. Since then the actor’s held memorable roles in True Detective, Interstellar, and White Boy Rick (which also premiered at Toronto this month).
After meeting Alves in 2006, she and McConaughey welcomed their first child in 2008 (Levi, 10) followed by Vida, 8, and Livingston, 5. They wed six months prior to the birth of their youngest child.