In 1996, she married her Hackers costar, Johnny Lee Miller, but broke up with him after three years. Only a few months later, she moved on with Billy Bob Thornton, whom she was married to from 2000 to 2003.
Jolie dated her third husband, Brad Pitt, for the longest time. They tied the knot in 2014 after nearly nine years of dating. However, they became legally single in 2019 following their split in 2016.
Billy Bob Thornton
The actor-director married Melissa Lee Gatlin in 1978 but called it quits in 1980. He then exchanged vows with Toni Lawrence in 1986 and stayed in their marriage until 1988.
In 1990, Thornton married Cynda Williams but divorced two years later. Before his marriage with Jolie, he was married to Pietra Thornton from 1993 to 1997.
Currently, he is enjoying his married life with Connie Angland, whom he married in 2014.
Drew Barrymore has had three husbands, with her first marriage to Jeremy Thomas only lasting less than two months. Her second with Tom Green also lasted a short time as they were only together for less than a year in 2001.
"I don't know how to date with kids, you know," she said. "I'm not there yet. I have two young girls, [ages 7 and 9] and I'm like, I don't want to bring people home."
Halle Berry knows what it is like to not have a relationship work out.
The Miss USA runner-up married former baseball player David Justice in 1993 but broke up in 1997. She then moved on to a two-year marriage with Eric Benét in 2001 and had another short-lived union with Olivier Martinez from July 2013 to 2015.
In 2017, Berry spoke up about fairy-tales in her interview with Entertainment Tonight.
"In every one of those situations, as hard — and sometimes embarrassing — as it was, I learned so much about myself. All of those relationships were necessary for me," she continued. "We all come here with lessons that we have to learn and those relationships provided me with lessons that got me to where I am right now."
Jackson split from her third and most recent husband in 2017, five years after they wed in 2012.
It took Kate Winslet two failed marriages before finding her third and current husband, Edward Abel Smith.
The famed Titanic actress married director Jim Threapleton in 1998 before calling it quits in 2001. She then married Sam Mendes in 2003, but their relationship was tested by infidelity allegations involving Rebecca Hall.
Mendes denied cheating on Winslet but ended up dating Hall a year after the Mare of Easttown divorced him.
Speaking about her first two failed marriages, Winslet told WSJ Magazine in 2015 that no one knew what happened in her life.
"No one really knows why my first marriage didn't last; no one knows why my second didn't," she said. "And I'm proud of those silences."
Kenny Rogers had five wives before he died in 2020.
The late singer's first marriage was with Janice Gordon. He married Jean Rogers from 1960 to 1963 before his next wedding to Margo Anderson from 1964 to 1976.
Rogers was married to actress Marianne Gordon from 1977 to1993. Four years later, he married his fifth and last wife, Wanda Miller, whom he spent his final days with.
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Kim Kardashian has yet to find her "final true love" after being married thrice.
She married Damon Thomas in 2000 when she was 20 years old and divorced in 2004. The KKW Beauty mogul had a 72-day marriage with Kris Humphries in 2011 before she tied the knot with her third husband, Kanye West, in 2014. They split in 2021.
got married eight times to seven women before his death in January 2021.
Between 1952 to 1967, the Larry King Live host was married to Freda Miller, Annette Kaye, Alene Akins and Mickey Sutphin. He wed Akins again in 1968, but the couple split again in 1971.
Five years later, King married and split in 1983. He was also married to from 1990 to 1992 before his nearly 22-year marriage with Shawn Southwick.
Lisa Marie Presley
Presley married Nicolas Cage in 2002, but their romance lasted only three months.
Lisa Marie's fourth and last husband was Michael Lockwood, whom she was married to from 2006 to 2016.
The late Night at the Museum actor Mickey Rooney got married eight times in his lifetime.
His first marriage was to Ava Gardner from 1942–1943. He then married Betty Jane Phillips (1944–1949), Martha Vickers (1949–1951), and Elaine Mahnken (1952–1958).
Rooney's fifth wife, actress Barbara Ann Thomason, was murdered by a stuntman and actor with whom she had been having an affair.
Following her death, Rooney moved on with her best friend Marge Lane, though their marriage lasted only 100 days.
The Breakfast at Tiffany's star was married to Carolyn Hocket from 1969 to 1975 before he wed Jan Chamberlin from 1978 to 2012.
Before finding his now-wife, , in 2021, Nicolas Cage married four other women in the past.
That same year, he started his married life with Alice Kim until they called it quits in 2016.
Pamela Anderson has been married to six times to five people, with her first wedding being with rocker Tommy Lee in 1998. After their short-lived marriage, they had an on-again, off-again relationship for years before her wedding to Kid Rock.
After her divorce from the musician, she married poker player Rick Salomon and had their union annulled in February 2008. She remarried him eight years later, but their relationship did not work out again.
Anderson's sixth marriage was with her bodyguard, Dan Hayhurst, which lasted two years, from 2020 to 2022.
Scarlett Johansson's Marriage Story seemingly mirrored her past weddings.
She started dating Colin Jost that same year, and they wed in October 2020.
In an interview with Vanity Fair in November 2019, Johansson opened up about her similarities with her character in the Oscar-nominated film.
"I understood the bittersweetness of it somehow, in a way," she said. "All those kind of in-between feelings that the character has. I understood them because I had gone through them myself."
Stevie Wonder's first marriage was with Syreeta Wright, which lasted from 1970 to 1972. After three decades, he exchanged vows with Kai Millard, though they broke up in 2009 and divorced for good three years later.
In 2017, the "Isn't She Lovely" singer married his third and current wife, Bracy.