14 Famous Co-Stars Who Played Love Interests More Than Once

Find out which stars have played love interests on multiple occasions…

1. Adam Sandler & Drew Barrymore

Throughout their careers, Adam Sandler and Drew Barrymore have gotten to work together on numerous occasions, including three films where they portrayed love interests — The Wedding Singer, 50 First Dates, and Blended. Looking back, Drew says their bond is “all based in like, love, admiration and humor” and she always knew she wanted to work with him.

“You know, I just always believed in him so much…Comedians create their own brand, their own flavor and scent and, you know, ideal around them, that is not easy to do,” Drew told People. “It’s like creating a tapestry that is so distinct unto themselves. And I was so there for what Adam Sandler was putting out into the wild that I just wanted to be next to it. I wanted some place to put my admiration and I thought a film was the most safe and cathartic place to do it.”

2. Timothée Chalamet & Saoirse Ronan

Timothée Chalamet and Saoirse Ronan are still young actors, but they’ve already had the chance to work together on three occasions. In two of those films, Lady Bird and Little Women, they even played love interests.

“I always knew he was very special. And he was very magnetic as an actor. We’ve always just felt very comfortable with one another,” Saoirse shared with Dazed in 2020. “We’re very different in the way we work and the kind of performances that we give, and that really excites me — how different we both are.”

She continued, “He’s someone who I want to continue to work with because I’m just quite interested to see how it goes. As we get older and when we have more and more experience, what it’s like when we come back together.”

3. Emma Stone & Ryan Gosling

Emma Stone has teamed up with Ryan Gosling on the big screen many times, playing love interests in Crazy, Stupid, Love, Gangster Squad and La La Land. While Ryan admits it can be tough working together at times because they’re both “such knuckleheads,” they definitely love their time on set.

“I can’t even imagine what my life would be without Ryan. He’s so special,” Emma said at the Telluride Film Festival. “It makes me emotional. He’s so talented but he’s such a great person to work with because he’s so collaborative and excited about the process. He’s taught me a lot about being really generous.”

4. Winona Ryder & Keanu Reeves

Winona Ryder and Keanu Reeves have had the chance to work together on four different films and have played love interests in three of them — Bram Stoker’s Dracula, A Scanner Darkly, and most recently, Destination Wedding. Keanu says that it just makes sense for them to work together considering they’re so similar.

“We like each other, personally, I think. And professionally, we have such a short hand because we have gone up against it and gone through the process many times. We’re both kind of cut from the same acting tradition cloth. So we view rehearsal the same, we review what a character is, we develop the scene together,” Keanu shared.

5. Matthew McConaughey & Kate Hudson

Matthew McConaughey and Kate Hudson are known for their starring roles in the rom-coms of the early 2000s so it only makes sense that they’ve worked together more than once. In fact, the duo played love interests in both How to Lose a Guy in 10 Days and Fool’s Gold. Looking back, Matthew says that when they first met, they were instantly comfortable with one another.

“We met on the Paramount lot. Those casting, meeting couches, especially for rom-coms are — you want to see the chemistry between the two leads. You want to see how the jive is. We’re not reading through the script, we’re not reading lines…Immediately we were comfortable with each other and we jived with each other,” he told People.

He continued, “We busted each other’s chops and we laughed a lot. And there was a bit of rock and roll exchange that [we thought], ‘Oh, this could be some heavyweight fun.’ And I think that’s why I was cast and that’s why, to whatever extent, it worked.”

6. Javier Bardem & Penélope Cruz

Penélope Cruz and Javier Bardem may be married in real life, but they’ve also appeared in eight films together. In four of those flicks, they played love interests — Jamón, Jamón, Vicky Cristina Barcelona, Loving Pablo, and Everybody Knows. Javier says that while they enjoy working together, they always have to be conscious of their real-life relationship.

“We work as hard as we can, but we recognize how hard we can work depends on each other’s needs. It’s important not to be confused by fiction. Fiction is fiction, reality is its own thing. When you’re younger — because we’ve worked together many times over the years, we met when I was 21 and she was 16 — you tend to confuse one for the other, or mix them. Now, I’m going to be 50 in a few weeks, and I don’t do this anymore. She’s the same way. You must always know when you’re working on a level of re-creation, outside of real life. Penélope and I, we have to protect the ‘us,’” Javier told Vulture.

7. Kristen Stewart & Jesse Eisenberg

Kristen Stewart had worked with Jesse Eisenberg several times throughout her career, including three films where they play love interests — Adventureland, American Ultra, and Café Society. While Jesse once joked that they keep getting paired together because Kristen lost a bet, she says

“I think we’re both just kind of weirdos. As a team, we’re a little bit less weird, because we get it from each other,” Kristen said on the Today show. “We’re like the nerds who as a whole actually become like, ‘Oh, we can make a cool movie together.”

8. Eugene Levy & Catherine O’Hara

Eugene Levy and Catherine O’Hara first met in the early 1970s when they were both members of Second City improv theater in Toronto. They became close friends and since then, they’ve had the chance to collaborate on numerous projects and have played love interests in Best in Show, A Mighty Wind, and Schitt’s Creek. Eugene says he believes their relationship works because they haven’t gotten wrapped up in Hollywood.

“I think we’re probably two of the un-show-busiest, un-show-business-iest kinds of people. I think we’ve always taken our work seriously, but you know, Catherine’s just a regular person. Like, you don’t get caught up in the trappings of the business that you’re actually in. And nothing has really changed in all of these years. Catherine hasn’t changed at all,” he told Vulture.

9. Jennifer Lawrence & Bradley Cooper

Jennifer Lawrence and Bradley Cooper have worked together on quite a few films, including Silver Linings Playbook and Serena, in which they play love interests. Jennifer joked that the secret to their success as co-stars is the fact that they keep their chemistry strictly on screen.

“I mean, any male role is going to make me think of Bradley because in my opinion, he’s the best, and I love working with him,” Jennifer shared before Bradley added, “I respect her so much as a professional, as an actor, and I think she’s the best there is. And I just learn from her. You always want to work with people that are better than you.”

10. Goldie Hawn & Kurt Russell

In real life, Goldie Hawn and Kurt Russell have been together for decades so they’ve enjoyed the chance to work side-by-side on multiple occasions. Through the years, they’ve played love interests in Swing Shift and Overboard as well as The Christmas Chronicles series. Looking back, Kurt says they’ve always been pretty selective about what they work on together.

“Goldie and I are pretty choosy. And generally, Goldie Hawn movies and movies that Kurt Russell is in are pretty different things,” Kurt told the New York Times. “It’s not mandatory just because you live with someone, you love someone, and you enjoy working together that you should do 10 or 15 movies together.”

11. Kate Winslet & Leonardo DiCaprio

Kate Winslet and Leonardo DiCaprio have played love interests in two films together — Titanic and Revolutionary Road — and have become great friends along the way. Looking back on the early days of their relationship, Kate says the pair “clicked immediately.”

“Once I started working with Leo, we were able to kind of find our own rhythm. And it’s amazing to kind of look back and think about it all over again,” Kate told ET. “He was this kind of mess of long, skinny, uncoordinated limbs. And he was just very free with himself, and he had this effervescent energy that was really magnetic. And I remember thinking, ‘Oh, this is gonna be fun. We’re definitely gonna get along.’ And we just really did. We just really did.”

12. Jennifer Aniston & Jason Bateman

Jennifer Aniston and Jason Bateman have teamed up on the big screen on many different occasions and have played love interests in both The Break-Up and The Switch. Jason once joked that he was actually blackmailing Jennifer into putting him in her films.

“We’ve always just really gotten along well. I think I was just fortunate to be a good fit for parts in her films,” Jason told The Guardian.

13. Amy Adams & Christian Bale

Amy Adams has worked with Christian Bale on several occasions, playing love interests in both American Hustle and Vice. Looking back, Christian proved to be a great co-star for Amy, explaining that he stepped in to be a “mediator” when she found herself in the middle of conflict with director David O. Russell on the set of American Hustle.

“I did what I felt was appropriate, in very Irv style,” Christian told GQ. “If I can have some sense of understanding of where it’s coming from, then I do tend to attempt to be a mediator. That’s just in my nature, to try to say, ‘Hey, come on, let’s go and sit down and figure that out. There’s gotta be a way of making this all work.’ You’re dealing with two such incredible talents there.”

14. Tom Hanks & Meg Ryan

Tom Hanks and Meg Ryan have played love interests in all four of their flicks together: Joe Versus the Volcano, Sleepless in Seattle, You’ve Got Mail, and Ithaca. Looking back on their years of working together so closely, Meg explained why they made such great co-stars.

“He’s just so easy. He listens; he roots for other people,” Meg shared. “He doesn’t like there to be drama. I feel the same way. We’re just really there to have fun, this is supposed to be a creative experience and there’s no reason to get heavy.”