On July 29, 2000, Brad Pitt and Jennifer Aniston, one of Hollywood’s highest-profile couples, marry at the Malibu, California, estate of the producer Marcy Carsey (The Cosby Show). The two actors reportedly met on a blind date in 1998 and quickly became favorites of the tabloid media once they went public with their romance. Their wedding cost an estimated $1 million and featured tight security to keep out the paparazzi.

Pitt, who was born in 1963 in Oklahoma, rose to fame in the early 1990s with roles in such films as Thelma & Louise (1991), A River Runs Through It (1992) and Kalifornia (1993). He went on to build a long list of starring movie credits, including Fight Club (1999), Ocean’s Eleven (2001) and Babel (2006). Aniston, who was born in 1969 in California, became famous for her role as Rachel Green on the hit TV sitcom Friends, which aired from 1994 to 2004. The actress has also made a number of movies, including The Good Girl (2002), Bruce Almighty (2003), Rumor Has It (2005), Wanderlust (2012), We're the Millers (2013) and Cake (2014).

Despite their reputation as one of Hollywood’s golden couples, rumors eventually began to circulate that Aniston and Pitt were having problems. In 2004, speculation swirled that Pitt had become romantically involved with Angelina Jolie, his co-star in Mr. & Mrs. Smith (2005). Over the New Year, Pitt and Aniston were photographed walking hand-in-hand on the beach in Anguilla, yet just days later, while they were still on vacation, a joint statement was issued announcing their separation. Though it seemed to be an amicable breakup, the press speculated that Pitt had wanted to have a family and Aniston–who had recently wrapped up a 10-year-run with Friends and had begun appearing in more films–was reluctant to take a break in her career for motherhood. Pitt was also depicted as being increasingly involved in global charity work, including the AIDS crisis in Africa.

Analysis of the breakup only intensified that spring, after Pitt was photographed with Jolie, a UNICEF representative, and her adopted son at a beach resort in Africa. Soon, they emerged as a full-blown couple, posing as a 1960s-era husband and wife (with a brood of blond children) for a 60-page photo spread titled “Domestic Bliss” in the July 2005 issue of W magazine. Outraged Aniston fans and friends denounced Pitt (who had in fact come up with the concept for the photo spread himself) as insensitive, and Jolie as a glamorous homewrecker. Novelty T-shirts at the time advertised their wearers as belonging to “Team Aniston” or “Team Jolie”; according to Vanity Fair, Aniston T-shirts outsold Jolies 25 to one.

Aniston and Pitt’s divorce was finalized in October 2005. In January 2006, Jolie announced she was pregnant with Pitt’s child; soon after, the news broke that Pitt had successfully adopted Jolie’s children Maddox and Zahara, whose surnames were legally changed to Jolie-Pitt. Pitt and Jolie divorced in 2016.