A near-perfect adventure movie (plus a few “kissing parts”), the fantastical 1987 film The Princess Bride is one of the most beloved movies of the decade. It’s a perennial favorite among children, their parents, and anyone looking for a story filled with comedy, drama, revenge, poisoning, murder, magic, and, yes, romance. The love between the young Princess Buttercup (the 20th most beautiful woman in the world) and the stable-boy-turned-dread-pirate Westley wouldn’t have hit nearly so hard if the filmmakers hadn’t cast the right actors in the roles. Relative newcomers Robin Wright and Cary Elwes turned out to be just that—and the film’s success set them up for long careers over the decades that followed. Want to know what they’ve been doing in the years since, and see them now, at ages 56 and 59? As you wish.
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Though Buttercup was Wright’s breakthrough role and remains one of her most iconic, The Princess Bride isn’t the only era-defining classic she appeared in. In 1994, she played the older Jenny in the Best Picture Oscar-winner Forrest Gump—one half of the duo (with Tom Hanks) who famously went together “like peas and carrots.” The performance earned her a Golden Globe nomination for Best Supporting Actress.
Wright worked regularly in film throughout the 1990s and early 2000s, often appearing alongside her partner and eventual husband Sean Penn. The two first appeared together in 1990’s State of Grace; 1995’s The Crossing Guard, which Penn also directed; 1997’s She’s So Lovely; and 1998’s Hurlyburly. She also acted in Penn’s 2001 thriller The Pledge, starring Jack Nicholson. Roles in movies Penn wasn’t involved in include Moll Flanders, opposite Morgan Freeman; M. Night Shyamalan’s superhero thriller Unbreakable, starring Bruce Willis and Samuel L. Jackson; White Oleander; and A Home at the End of the World. Wright also performed motion capture for the 2007 animated version of Beowulf, re-teaming with Forrest Gump director Robert Zemeckis.
Hot off of his winning performance as Westley, Elwes continued acting in the wake of The Princess Bride‘s success, next appearing in the comedy Never on Tuesday and the Oscar-nominated 1989 Civil War drama Glory.
Throughout the ’90s, Elwes acted opposite a young Tom Cruise in 1990’s Days of Thunder, and landed roles in Bram Stoker’s Dracula; Kiss the Girls; Twister; The Crush, co-starring Alicia Silverstone; and Cradle Will Rock. He kept very busy in the ’00s with roles in Shadow of the Vampire, Georgia Rule, and A Christmas Carol—not to mention several films in the Saw horror franchise.
For most of the last decade, Elwes has continued to work in a string of lower-budget indie films, but he found new fans in a major way in 2019 with his performance as the amoral mayor of Hawkins, Indiana in the third season of the Netflix megahit Stranger Things, a role written with him in mind.
Elwes had a blast on the show—”I was thrilled from one day and I’m still thrilled today,” he told Vulture—and indicated his willingness to return if he were asked.
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Though she’s continued working in films, recently appearing in Blade Runner 2049 and in multiple movies in the DC Extended Universe as Wonder Woman’s aunt Antiope, Wright has spent the majority of her time over the last decade acting for the small screen, starring in six seasons of Netflix’s early streaming smash House of Cards. She played Claire Underwood, the wife of scheming U.S. Congressman Frank Underwood (Kevin Spacey) and an equal partner in his bloodstained march to the White House.
In fact, when Spacey was fired and written off in the wake of several sexual assault allegations (he maintains his innocence), Wright took over as the sole lead for the final season, in which Claire ascended to the Oval Office herself.
“Kevin and I knew each other between ‘action’ and ‘cut’ and in between setups where we would giggle,” she told NBC’s Today of Spacey’s fall from grace. “I didn’t know the man. I knew the incredible craftsman that he is.”
There was talk of canceling the series, but Wright fought for it. “I was just like, ‘No, no, no. It’s not right. This is a job, and we’re going to finish it out as we intended,” she told the outlet. House of Cards ended in 2018.
For an entire generation of viewers, Elwes is synonymous with his role in The Princess Bride, so it’s only fitting that he literally wrote a book on it. In As You Wish: Inconceivable Tales from the Making of The Princess Bride, published in 2014, he gives his personal perspective on the making of a classic and shares stories from his fellow cast members.
Far from revealing scandals from the set, the book shows that the film’s production seemed charmed from the start: The cast came together just so, everyone got along fabulously, and the movie became one fans pass down to their kids. “We had a really fun time working together on the film,” Elwes wrote of his on-set relationship with Wright. “With myself as a pirate. And she as a fair maiden. Running off together in the spirit of love and adventure.”
While she isn’t exactly a tabloid fixture, Wright’s personal life has made some headlines over the decades. She has been married three times, most prominently to fellow actor and frequent screen partner, Penn. The pair met while acting together in State of Grace in 1990 and then married in 1996, after a few brief breakups and the birth of their two children, daughter Dylan Frances (born April 1991) and son Hopper Jack (born August 1993).
Over the next decade-and-a-half, Wright and Penn would separate, announce plans to divorce, and then reconcile multiple times before finally officially severing their union in June 2010.
Previously married to actor Dane Witherspoon from 1986 to 1988, Wright was briefly engaged to actor Ben Foster and then married San Laurent fashion executive Clément Giraudet in 2018. Wright filed for divorce from Giraudet in September of this year.
Elwes mostly keeps his personal life quiet. He’s been married to the same woman, photographer Lisa Marie Kurbikoff, since 2000, and they have one child, a daughter.
Though born in England, the actor has recently been active in U.S. politics. In 2020, amid the pandemic lockdowns and the run-up to the presidential election, he hosted a virtual reunion during which surviving members of the cast performed a read-through of the script alongside guest stars including Josh Gad, who took over the role of the giant Fezzik from the late Andre the Giant. The event raised more than $4 million for the Democratic Party.
Though Wright is still acting—she recently signed on for a role in the Netflix fantasy film Damsel, from director Juan Carlos Fresnadillo (28 Weeks Later) and starring Millie Bobby Brown—she’s also working behind the camera. In 2021, she released her directorial debut, Land, in which she also stars as a woman who flees from her responsibilities to live in the Rocky Mountains, nearly dies, and is saved from death (spiritually and literally) by a local hunter. The film premiered at Sundance and earned largely positive reviews.
Wright (pictured above with daughter Dylan) has also worked in this capacity on television, directing two Season 4 episodes of the Netflix crime series Ozark and, previously, multiple episodes of House of Cards.
The actor/director would like to see other women in Hollywood follow in her footsteps. “Should I? Can I? Yes, you can. You can do it,” she said in a 2021 interview with CBS News, speaking to other performers who might dream of one day stepping behind the camera. “You just have to be committed to your strength and your confidence that you can do it.”
Perhaps thanks to the career boost from Stranger Things, Elwes will next appear in two big-budget Hollywood productions. He will reunite with his Days of Thunder co-star Cruise in next year’s Mission: Impossible—Dead Reckoning Part I playing an undisclosed role. “The film is extraordinary, the scale of it is amazing,” the actor told SiriusXM Radio. “It was the first time Tom and I had worked together in 31 years—we did the math—and honestly, he hadn’t changed at all. The guy was unbelievable, the way that he works, the focus.”
Elwes will also appear in the next film from comic book director Zack Snyder. Rebel Moon, due out from Netflix next year, is a sci-fi thriller about a human colony surviving at the edge of space. A sequel has already been green-lit.
