#TBT: Check in every Thursday as we throw it back to some of our favorite celebrity couples of all time.
Who: Actor and Oscar-winning producer Brad Pitt, 54, and Oscar-winning actress and lifestyle boss Gwyneth Paltrow, 45.
How they met: Brad and Gwyn bonded on the set of David Fincher thriller Se7en (you know the one) in 1994.
Why we loved them: They both earnestly thought it would be a good idea to get matching haircuts:
When they peaked: See photo above.
The breakup: Brad proposed after dating Gwyneth for two years in December 1996. They were totally crazy about each other (matching haircuts and all), but six months later, the flame had dimmed. Though the split was initially shrouded by mystery, in the years (decades!) to come, Paltrow has given us some insight.
In 2015, the Goop goddess spoke with Howard Stern about her failed relationship with Pitt, explaining, “I was such a kid. I mean I was 22 when we met and it’s taken me until 40 to get my head out of my ass. You can’t make a decision when you’re 22 years old ... I think I was a kid and I wasn't ready, and he was too good for me."
Speaking with Sophia Amoruso on an episode of the Girlboss podcast in 2017, Paltrow revealed her propensity to “f—k up” relationships. “Oh my God, I’ve f–ked up so many relationships,” she said. “I’m a pretty good friend and sister and daughter, but I am at my potentially most vulnerable and f–ked up in the romantic slice of the pie.” When Amoruso made mention of Pitt, Paltrow responded, “I f–ked that up, Brad!”
Where they are now:
Not long after the split, Pitt began dating sitcom star (and InStyle cover girl) Jennifer Aniston. The pair wed in 2000 and remained legally bound until 2005, which was shortly followed by the donning of the age of Brangelina (Pitt and fellow actor Angelina Jolie). He and Jolie stayed together for over a decade, calling it quits in September 2016; they share six children.
Outside of the media firestorm that dominated Pitt’s personal life, his professional life stayed on a (mostly) upward trajectory. The actor found success with films like Fight Club (1999), Ocean’s Eleven (2001), Babel (2006), and The Curious Case of Benjamin Button (2008). Pitt’s production company Plan B Entertainment made immense gains through the years as well—in 2014 he scooped up a Best Picture Oscar for 12 Years a Slave.
After calling off her engagement to Pitt, Paltrow got involved with another A-list actor: Ben Affleck, with whom she stayed with until 2000. In 2002, just weeks prior to the death of her father Bruce, Gwyneth began dating Coldplay frontman Chris Martin. The pair wed in 2003 and went on to have two children together (Apple, 14, and Moses, 12). In 2014, Gwyneth coined the relationship term of the century after announcing that she and Martin had “consciously uncoupled.” Today, Paltrow is preparing to wed her TV writer/producer fiancé Brad Falchuk.
On the professional front, Paltrow has thrived over the past 20 years. She won an Oscar for her performance in Shakespeare In Love in 1999, and went on to star in acclaimed films like The Talented Mr. Ripley (1999), The Royal Tenenbaums (2001), and Proof (2005). In 2008, Paltrow took a step back from acting to launch her wildly popular lifestyle brand Goop, which soon evolved from a newsletter to a website, an e-commerce site, and a print magazine.