The Most Iconic Hollywood Romances of All Time

We've had our fair share of celebrities dating each other throughout the last several decades, but there's a special category for that pairing that you love to see, either because you can't believe it happened, you love them together, or you just want to see how it all shakes out. In order to be considered an iconic Hollywood couple, you need a few things. Firstly, both people need to be at least relatively famous—the coupling of them together raises their profile and they start to be known as a "power couple" by friends and the media alike. Secondly, and this doesn't always need to be the case but it certainly doesn't hurt: The more drama, the more fans are interested in the union. Lastly, the celebrity couple should be together for several years. Ultimately, whether they remain together or not, their relationship should have had some staying power to be truly considered iconic.

Ahead, these are 32 of the most iconic Hollywood couples of all time—be they actors, singers, artists, writers, or other performers, their unions made everyone fascinated.

Sarah Michelle Gellar and Freddie Prinze Jr

Even though they met on the set of I Know What You Did Last Summer, the pair didn't start dating right away (actually, they didn't really get along, lol). They went on an "accidental" date in 2000 (their third invitee bailed) and things escalated quickly: They got engaged in 2001 and married in 2002. At the time, Gellar explained, "We are each other's best friend...He is my first love." In the midst of children and pets (and a lot of fun Instagram posts), the two celebrated their 20th anniversary in 2022.

Reese Witherspoon and Ryan Phillippe

Basically the "it" couple of the '90s (fans could not get enough of the pair) Reese Witherspoon and Ryan Phillippe starred as doomed love interests in Cruel Intentions. They actually met beforehand at Witherspoon's birthday party in 1997, got engaged in 1998, and married in 1999. The two were semi-open about their relationship (Phillippe famously quipped to Witherspoon when they presented at the 2002 Oscars, "You make more than I do, so go ahead," which was apparently unscripted). Fans weren't that surprised when the two divorced in 2008, but that doesn't mean we weren't devastated all the same.

Antonio Banderas and Melanie Griffith

This Hollywood power couple lasted two decades, making them a beloved pairing in the '90s and '00s. They costarred in 1995's Two Much, while both married at the time to other people. After their divorces were finalized, they got married one month(!) later in 1996. With some ups and downs—including Madonna's interest in Banderas while the two were shooting Evita and Griffith's struggles with addiction—the two announced their split in 2014. Banderas did tell Entertainment Tonight in 2018, though, that "I will love that woman until the day I die."

Lisa Bonet and Lenny Kravitz

In case you only know them as the parents of Zoë Kravitz, you maybe didn't live through their heyday: Lenny Kravitz and Lisa Bonet, who were married from 1987 to 1993 were the couple that dressed well and seemed utterly cool. They met in 1985 backstage at a New Edition concert. In his memoir, Kravitz explained, "We vibed immediately. Time stood still. Without a lot being said, there was magnetism. I'd never had an encounter like it before. We were from the same tribe." After their divorce, the two apparently remained, as Kravitz put it, "best friends."

Demi Moore and Bruce Willis

These two really popularized the notion of "bring your boyfriend to the red carpet and get people excited by the sight of you together." The power couple of the '80s and '90s, the two met (where else?) at a screening of 1987's Stakeout and literally got married the same year, four months after they met. They were a pretty public couple, even working together professionally, so fans were crushed to hear that they were splitting. Despite their divorce in 2000, the two apparently remained friends and in each other's lives.

Gwyneth Paltrow and Brad Pitt

Even though they were only together between 1994 and 1997, the iconic couple (who had...exactly the same haircut) were a huuuuuge power couple at the time. They met while filming Se7en and started dating basically immediately, with Pitt telling Rolling Stone, "I knew immediately...I got within 10 feet of her, and I got goofy. I couldn't talk." They actually got engaged in 1996, then split six months later. According to Paltrow, there's no bad blood between the pair. In a 2022 interview on Goop's website, the pair said they were glad to be friends and loved each other. Aw!

Ellen DeGeneres and Portia de Rossi

When Ellen DeGeneres and Portia de Rossi met backstage at a Rock the Vote event in 2001, it was love at first sight—but de Rossi wasn't "out" yet. She told Oprah in 2009, "It took me three years to actually tell her how I felt about her because I was on Ally McBeal at the time and I was not living as an openly gay person. I was closeted and very, very afraid that if I talked about being gay, it would be the end of my career. So, I wasn't about to date the most famous lesbian in the world." The two would later reconnect in 2004, and DeGeneres said they were "soulmates." They married in 2008 and renewed their vows in 2023.

Barbra Streisand and Elliott Gould

Barbra Streisand and Elliott Gould, two up-and-coming actors, met while being cast as the leads in the 1962 Broadway show I Can Get It for You Wholesale. They had an instant connection, and the two wed in 1963, welcoming a son in 1966. The two met before they achieved icon status professionally (and unfortunately the press gave Gould the nickname "Mr. Streisand" because of Steisand's fame, which, ouch). They divorced in 1971; Streisand's ambition and fame was a big part of the reason, apparently. The two became more civil over time, but in 1970 Gould infamously said that the marriage "had a lot of chocolate souffle and things like that, but it was also like a bath of lava."

Brad Pitt and Jennifer Aniston

In the late '90s, no couple was more exciting than Brad Pitt and Jennifer Aniston, who began quietly dating in 1998 but then took their relationship public at Pitt's Fight Club movie premiere. They got married the following year in 2000, but (after rumors that Pitt was getting romantic with his coworker Angelina Jolie on the set of Mr. and Mrs. Smith) separated early in 2005. Despite an intense amount of drama and scrutiny around that particular love triangle, Pitt and Aniston reunited briefly at the 2020 SAG Awards—clearly delighted to catch a glimpse of each other.

Will Smith and Jada Pinkett Smith

A highly public couple, Will Smith and Jada Pinkett Smith have been open about their relationship in the spotlight for decades. They met on The Fresh Prince of Bel-Air in 1994 (Smith was married at the time) but the two began seeing each other that year when Smith was separated. The two married in 1997 while Pinkett Smith was pregnant with their first child; Over the years, they weathered rumors of cheating and having an open marriage, among others. Following much attention after Smith slapped Chris Rock during the 2022 Oscars, in her 2023 memoir, Pinkett Smith said she and Smith had been separated since 2016.

Ryan Gosling and Rachel McAdams

It may surprise you to learn that, despite some intense chemistry on screen in The Notebook, that Ryan Gosling and Rachel McAdams did not care for each other at first. (Allegedly, Gosling asked if they could replace McAdams with someone else, while they were literally filming a scene.) Then—twist!—the two started dating in 2005 and broke up in 2007. But despite the shortness of their time together, people reaaaally loved their pairing: Gosling blamed show business and admitted to GQ in 2007 that "Women are mad at me" for him breaking up with her.

Ben Affleck and Jennifer Garner

Fresh off the heels of a split with another Jennifer (Jennifer Lopez), Ben Affleck quickly began seeing Daredevil costar Jennifer Garner in 2004; Technically they'd met on the 2000 film Pearl Harbor, but Garner was married at the time. Affleck and Garner got married in 2005 and were together for a decade before announcing their separation in 2015. They divorced in 2018 but remained in each other's lives as co-parents; Affleck called the split "the biggest regret" of his life in 2020 and attributed a portion of their breakup to his struggles with addiction. He also infamously said, "[Marriage] is work" (lol) in his 2013 Oscars speech.

Gisele Bündchen and Tom Brady

Gisele Bündchen said that when she met Tom Brady in 2006, she knew "the first time" she saw him that the pair had a special connection. The two weathered ups and downs, including Brady's ex Bridget Moynahan's pregnancy in 2007, but got engaged and married in 2009. After a long, pretty public union, Brady announced his retirement in 2022 and then swiftly returned to football. Rumors began to swirl that the two were living apart and had hired divorce lawyers because they weren't seeing eye to eye over that decision. They announced their split later that year.

Jerry Hall and Mick Jagger

One of the more dramatic couples on this list, the model and musician met in 1976, both with other people, and their relationship overlapped with Jagger's then-marriage. Jerry Hall and Mick Jagger got married (although not in a way that was legally binding) in 1990, and there were a lot of ups and downs including infidelity and breakups and an extramarital pregnancy. All told, the two were off and on for more than two decades, and continued to talk after their split.

Jack Nicholson and Anjelica Huston

Did you know that these two dated for 17(!!) years? The two immediately sparked a connection at Nicholson's 1973 birthday party, spending the night together and moving in together right away. The two apparently discussed marriage and tried to have children, according to Huston, and fans loved how normal they seemed—aside from the random acts of extreme gifting, like Nicholson reportedly giving Huston an elephant for her birthday. But infidelity on Nicholson's part, and his admission to her in 1989 that his mistress was pregnant, meant the end of their coupling.

Humphrey Bogart and Lauren Bacall

Meeting on the set of 1944's To Have and Have Not, Lauren Bacall and Humphrey Bogart started an infamous love affair (Bogart was still married at the time) that led to the pair getting married 11 days after his divorce—Bacall was 20, Bogart was 45. Despite potential emotional affairs and Bacall putting her career to the side, the pair were married for 11 years until his death in 1956. In her memoir, Bacall wrote, "No one has written a romance better than we lived it."

Robert Pattinson and Kristen Stewart

Playing two of the most fan favorite love interests ever (that's Bella and Edward from Twilight, in case you missed it), Kristen Stewart and Robert Pattinson took their relationship off-screen in 2009—making fans everywhere delighted. They dated for three years until paparazzi photos were released of Stewart kissing director Rupert Sanders. After that breakup, the pair briefly reunited before breaking up again. Stewart would later say to Harper's Bazaar UK in 2019, "When me and Rob were together, we did not have an example to go by. So much was taken from us that, in trying to control one aspect, we were just, like, ‘No, we will never talk about it. Never. Because it’s ours.'"

Ben Affleck and Jennifer Lopez

The timeline of Ben and Jen (known as "Bennifer" to fans) spans decades. The two originally met in 2002 on the set of Gigli and had a much-publicized relationship—they recounted that they were hounded by paparazzi—that apparently played a big part in their breakup in 2004. The two remained close...so much so that after J. Lo split with Alex Rodriguez in 2021, the two began "spending time" together, dating officially that same year, then getting married in 2022. J. Lo said to People that year, "I feel so lucky and happy and proud to be with him...It's a beautiful love story that we got a second chance."

Beyoncé and Jay Z

Beyoncé first met Jay Z when she was 18 and they began dating when she was 19. They first collaborated on "03 Bonnie and Clyde," which was the start of a long personal and professional collaboration. The pair became one of Hollywood's iconic couples and, despite ups and downs including infidelity, celebrated 15 years of marriage in 2023. In the 2013 Life Is But a Dream, Bey explained after they had their first child, "This baby has made me love him more than I ever thought I could love another human being...It's just that I love him so much that we almost feel like one. I don't know how to describe it."

Sonny and Cher

The performing duo lived their life in the public eye, so fans knew (or at least thought they knew) everything about Sonny and Cher's relationship. The age difference was pretty significant (Cher was 16 when they met and almost 12 years his junior), but they didn't start dating until she was a little older. Their career and partnership skyrocketed with "I Got You Babe" in 1965; The two wed in 1969 and started The Sonny & Cher Comedy Hour in 1971. The two would divorce in 1975 (Cher would cite infidelity and it was a contentious split), and would continue to have public ups and downs, but Cher read the eulogy at Sonny's funeral in 1998.

Angela Bassett and Courtney B. Vance

Angela Bassett and Courtney B. Vance wed all the way back in 1997. Initially meeting at Yale in the '80s, the two didn't date until the '90s when both were single. The two have spoken to the media about their relationship, with Bassett saying on their anniversary in 2022, "Thank you God for each and everyone [sic] one of these 25 years! We can’t wait to do 25 more!" They also literally wrote the book on love: called Friends: A Love Story, which they wrote together in 2007.

John Legend and Chrissy Teigen

Often described as the funniest Hollywood power couple, the singer-songwriter-musician and model-TV personality met in 2006 on Legend’s “Stereo” music video. They "closed the deal" right away, romantically speaking, according to Teigen, who's never been shy about sharing details of their love. Fans obsessed over their union, and both Legend and Teigen spoke about each other on social media and to the press. "I’m her biggest cheerleader. I always think she should do more," Legend told Vanity Fair in 2019.

Blake Lively and Ryan Reynolds

Even though Blake Lively and Ryan Reynolds met on set, via the much-panned Green Lantern, the two were in relationships with other people at that point. Both single in 2011, the two went out on a double date—with other people—and couldn't deny their connection to each other. The couple began dating in late 2011, and got married in 2012. The two shared (sometimes hilarious) bits and pieces of their relationship over the years, with Lively telling Vogue in 2014, “Everything we do in life, we do together...He’s going to be a great father and leader and patriarch—he’s so meant to be all of those things.”

Annette Bening and Warren Beatty

Warren Beatty actually cast wife-to-be Annette Bening in his 1991 movie Bugsy. She told People in 2022, "Wow, this guy is so smart and so sharp and funny, but more—just articulate." She remembers him charming, and he apparently felt the same way: Apparently he told the film's director that "I'm going to marry her" after the two first met. They kept very private about their union and their family, but Beatty told the Today show in 2016, “The most important thing that’s ever happened—the best thing that’s ever happened to me—was Annette and having four kids."

Tom Hanks and Rita Wilson

Hanks and Wilson first met in 1981, on the set of Bosom Buddies (a sitcom starring Hanks). He was married, but they connected as friends immediately. In their first feature film together, 1985's Volunteers, there was immediate chemistry. The two went public in 1986 (Hanks' divorce was finalized in 1987), and they got married in 1988. "The success of our relationship was a matter of timing, maturity and our willingness to have an intimate connection," Hanks told Oprah. "When I married Rita, I thought, 'This is going to require some change on my part'...In real life, our connection is as concrete as me sitting here."

Penelope Cruz and Javier Bardem

In 1992, Cruz and Bardem met on the set of Jamón, Jamón (Cruz was only 16, so Bardem later noted that despite their obvious chemistry nothing happened), and the two reunited in 2008's Vicky Cristina Barcelona. The two married in 2010—they have both mostly remained quiet about their relationship, but continued to act together (including in 2017's Loving Pablo and 2018's Everybody Knows) with the occasional red carpet appearance. Both were nominated for Oscars in 2022!

Victoria and David Beckham

When a soccer (football) star and a former Spice Girl started dating, it made fans absolutely obsessed. The pair met in 1997 (Victoria said it was love at first sight), got engaged and pregnant in 1998, married in 1999 and renewed their vows in 2006—David apparently surprised Victoria with the gesture, which included a private jet and their closest family members. The two weathered ups and downs (including rumors of infidelity) and celebrated their 20th anniversary in 2019.

Kurt Russell and Goldie Hawn

Originally meeting in 1968 on the set of The One and Only, Genuine, Original Family Band (Hawn's actually six years older, and he was only 16 when they originally met), the pair reconnected in 1983 on Swing Shift. When they got together as adults, both having been through divorces, the pair became one of Hollywood's most iconic and long-lasting couples. Hawn would tell CNN in 2023 that the two had no plans to get married, saying, "Because we had been married...And because when it doesn't work out, it ends up to be a big business. Somebody has to own something. It's always ugly."

Elizabeth Taylor and Richard Burton

They were the Hollywood couple: The paparazzi hounded them, and so did fans. Both were married at the time that they met, and their affair became international news (and dominated the coverage of the movie they met on, Cleopatra). They spent millions, particularly on jewelry and art. They battled addiction and affairs. They were divorced, then remarried, then divorced. And their love apparently outlasted it all—all the way to the last letter Burton sent Taylor, a few days before he died in 1984.

Iman and David Bowie

Married from 1992 until his death from cancer in 2016, Iman and Bowie were extremely private about their long-lasting marriage. According to Iman, speaking to the New York Times in 2021, both of them wanted a life away from the public and a life of purpose. The two managed to do just that, mostly living in New York and raising their daughter together. In 2022, she told Hoda Kotb that she thinks of him "every day, and every minute."

John Lennon and Yoko Ono

At Ono's solo art exhibit in 1966, she would meet John Lennon—and, even though Lennon was married, the two began an affair. Falling in love with her, he said, was different than anything he'd ever known—"more than a hit record, more than gold, more than everything." The two married in 1969—the same year the band split, which meant Ono faced accusations of "breaking up the Beatles"—and they would collaborate musically and as activists. After a brief separation and subsequent vow renewals, the couple stayed together until Lennon's murder in 1980.

Paul Newman and Joanne Woodward

In his memoir, Newman explained that he never felt sexy until he met his wife: "Joanne gave birth to a sexual creature. We left a trail of lust all over the place." Both were understudies for the 1953 play Picnic, and (even though Newman was married) the pair couldn't fight their connection. He and Woodward married shortly after his divorce in 1958; The pair had three daughters together and remained together, despite their self-professed ups and downs, until his death in 2008.