To certain pop culture fanatics, one of life’s greatest mysteries is as follows: How the hell does a scrawny curmudgeon like Sean Penn continually bag such hot chicks? From his stunning ex-wife Robin Wright to bombshells like Scarlett Johansson, the Oscar-winning actor seemingly can’t be without a beautiful woman at all times.
To others, it’s not a mystery at all: For reasons that are largely intangible, even the most intelligent, self-possessed women have fallen for classic bad boys at some point, and none are as historically bad as Penn.
Couple his notorious run-ins with paparazzi, lengendary hot temper, and jail time with his insane talent, political activism, brooding persona, and it’s not that hard to see why starlets are drawn to the 54-year-old.
Despite having been married twice, the public—and Penn himself, it seems—thought Charlize Theron was the real thing. Not only did he publicly refer to her as the love of his life, but the pair were reportedly on track to tie the knot until Theron reportedly broke things off in June 2015.
Now, Us Weekly is reporting that the actor is already rebounding with former “Friday Night Lights” actress Minka Kelly, whom he reportedly took to dinner in Napa, California, to celebrate her 35th birthday less than two week after his split with Theron.
Since keeping up with Penn’s romantic life is a full-time job, we’ve rounded up all the women the actor was married to, dated, or maybe dated.
Penn and actress Elizabeth McGovern—his co-star in Racing with the Moon—were engaged in 1984, but she broke it off. McGovern now stars as Lady Cora on "Downton Abbey."
Sean's most memorable union was with Madonna–they were married from 1985 to 1989—and was notoriously contemptuous. Between rumors of domestic abuse and jail time for Sean, it's pretty shocking he managed to snag so many other strong, gorgeous women after that.
Sean and "House of Cards" star Robin Wright started dating in 1990 before having to children then tying the knot in 1996. Their relationship was famously rocky, and despite several breaks, they divorced for good in 2010.
Rumor has it Penn dated folk-pop singer Jewel while on a break from Robin in 1995. Penn also directed Jewel’s music video for the song “You Were Meant For Me.”
According to the New York Post, Sean and Aussie supermodel were seen getting cozy at a swanky restaurant in New York in 1996. "They kept going up to the bar, the only place you can smoke in [restaurant] Coco Pazza,'' a patron told the Post. "They kissed between puffs, and acted like no one else was in the room.''
Penn dated supermodel and activist Petra Nemcova while on a break from wife Robin Wright in 2008 and was seen with her again in 2012.
After filing for divorce from wife Robin Wright in 2009, Sean wasted no time stepping out with swimsuit model Jessica White.
According to Star, Penn and Natalie Portman were caught making out at the Sunset Towers in Los Angeles in 2009. The spy was returning from the bathroom, and told the mag: "I had to go through some curtains — and that's when I interrupted Sean and Natalie!" the source reports. "When they saw me, they were startled and quickly composed themselves."
Though photos of them together are scarce, Scarlett and Sean—who have a 24-year age difference—dated in 2011, following her divorce from Ryan Reynolds.
After Scarlett, Sean moved onto Shannon Costello, the 26-year-old former communications director of his J/P Haitian Relief Organization.
Despite having called her the love of his life, Penn and Charlize Theron broke off their engagement in June 2015. The pair got together in December 2013, and sources say Theron, 39, was the one to break things off.
A source told Us Weekly that less than two weeks after splitting from fiance Charlize Theron, Sean Penn took actress Minka Kelly and a friend to dinner for her 35th birthday at Thomas Keller's elite restaurant The French Laundry in Napa, California. "That was their first date, but it was a group setting," the insider tells Us of the birthday feast at French Laundry. "It was more of a 'let's see how this goes.'"