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.

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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.

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