Angelina Jolie or Billy Bob Thornton — Who’s Been Married More Times?

Hollywood has its fair share of unusual exes. Consider the pairing of Angelina Jolie and Billy Bob Thornton, who engaged in strange antics both while they were a couple and after their split. And each was married both before and after their divorce.

With 20 years of difference in their ages, it’s easy to see why Thornton is the one with more marriages under his belt. He’s been married six times, while Jolie has been married half as many. 

Angelina Jolie and Billy Bob Thornton’s marriage 

Jolie and Thornton are one of many celebrity couples who eloped in Las Vegas. They barely even dated before their 2000 nuptials. With Jolie in jeans, according to Daily Mail, and Thornton wearing a hat, it’s safe to say this Vegas wedding was a seemingly spur-of-the-moment, casual affair. Following the low-key ceremony, the marriage lasted a couple of years, separating in 2002. They divorced officially in 2003.

The pair met while filming their movie Pushing Tin, quickly developing feelings for one another. So much so that even though Thornton was engaged to Laura Dern at the time, he still married Jolie. 

Although they were not on speaking terms after their divorce, Jolie later expressed to Vanity Fair that Thornton was a good man, and they shared a lot of laughs. He was simply not ready for the adoption process she went through with her son, Maddox, especially after already having three children.

Who were Jolie and Thornton’s former spouses?

Before their marriage, Thornton had been divorced four separate times. Jolie, meanwhile, had experienced one failed marriage of her own. Three of Thornton’s prior marriages lasted only two years each — from 1978 to 1980 with Melissa Gatlin, 1986 to 1988 with Toni Lawrence, and 1990 to 1992 with Cynda Williams. He and his fourth wife, Pietra Thornton (formerly Cherniak), were married for four years, from 1993 to 1997. 

Thornton had children with two of his former wives. He shares two sons with Cherniak and one daughter with Gatlin. 

Jolie was married to actor Jonny Lee Miller for three years. They wed in 1996 and divorced in 1999. However, the two remained amicable, with a source close to Jolie even reporting to People that one of her children was friends with his son. They’ve even gotten together on occasion for playdates. 

Jolie and Thornton both married again in 2014

Jolie and Thornton each went on to get married again in 2014, nearly 11 years after their split. Jolie married Brad Pitt, although they, too, ended their marriage a few years later. They share six children, including Maddox, who Jolie adopted at the end of her marriage to Thornton. 

Jolie has since remained single since her third divorce. Thornton, on the other hand, began dating Connie Angland following his split from Jolie. After more than a decade together, they tied the knot. Angland and Thornton share a daughter, Bella.