Winona Ryder and Keanu Reeves are getting together in Destination Wedding, but it’s not the first time they’ve played love interests. The first came in 1992, when the two got married on-screen (possibly for real) in Bram Stoker’s Dracula. Then 14 years later they played paranoid future-tweakers in A Scanner Darkly. (We’re not counting The Private Lives of Pippa Lee where they shared no screen time together.)
Now, in Destination Wedding, Reeves and Ryder play two strangers on their way to the same big nuptial ceremony in Californian wine country. Their cynicism for the whole affair (oh, you Gen Xers!) pushes them closer and as the weekend stumbles on, they just might discover that together they’re the greatest gift left off the registry.
Before the movie opens Friday, we’re looking through film history for the actors who have played couples more than three times on screen! We’re only including movies where the pair are in pursuit, together, or exes, and we’re not including sequels, so each character is unique. So who’s the Freshest couple? Who’s the most Rotten? And who’s been together on-screen for the longest time? It’s time to take a dive into the sea of love.
Allen and Keaton displayed immediate chemistry in their first pairing, the Herbert Ross-directed comedy Play It Again, Sam. A legendary run in comedy ensued, with Keaton acting as muse as Allen shifted from broad comedies to Best Picture-worthy films. Even later throwaway movie Manhattan Murder Mystery would turn out to be an enduring bon mot.
To Have and Have Not (1944) : 97%
The Big Sleep (1946) : 96%
Dark Passage (1947) : 92%
Key Largo (1948) : 97%
The 44-year-old Bogart met Bacall, just 19 at the time, on the set of To Have and Have Not. A whirlwind romance commenced and the pair got married in 1945, subsequently embarking on three noir masterpieces together: Key Largo, Dark Passage, and The Big Sleep. Though they never made any more movies together, they remained married until Bogie’s death just 10 years later in 1957.
Zelig (1983) : 100%
A Midsummer Night's Sex Comedy (1982) : 75%
Broadway Danny Rose (1984) : 100%
Shadows and Fog (1992) : 50%
Hannah and Her Sisters (1986) : 93%
Crimes and Misdemeanors (1989) : 93%
Husbands and Wives (1992) : 95%
As Allen and Keaton’s real-life relationship came to an amicable conclusion in the late-’70s, Allen would find his new muse for a new decade with Mia Farrow, which would go on to end under significantly less friendly terms. But until then, Farrow would be involved with his best films made in the ’80s, a rough time for most established filmmakers who weren’t Spielberg. Crimes and Misdemeanors and Hannah and Her Sisters are classic dramas at this point, and go some way to making up for curios like Shadows and Fog and Midsummer Night’s Sex Comedy.
Flying Down to Rio (1933) : 100%
The Gay Divorcee (1934) : 100%
Roberta (1935) : 83%
Top Hat (1935) t: 100%
Follow the Fleet (1936) : 80%
Swing Time (1936) : 100%
Shall We Dance (1937) : 88%
Carefree (1938) : 50%
The Story of Vernon & Irene Castle (1939) : 71%
The Barkleys of Broadway (1949) : 64%
Astaire and Rogers made a whopping 10 movies together in various stages of love, the most films out of any couple featured here, though that’s a byproduct of an era when it was common for Hollywood studios to contract “own” actors and actresses. Despite the mercenary nature of their roles, some of the movies Fred and Ginger made together are classics, with four rated a 100% on the Tomatometer. The two reunited after 10 years apart in 1949’s The Barkleys of Broadway, their only MGM musical (they had been under contract with RKO) and only time together filmed in color.
Pillow Talk (1959) : 92%
Lover Come Back (1961) : 89%
Send Me No Flowers (1964) : 57%
Day shared the screen with some of the biggest stars of the day, including James Stewart and James Garner. Her most fruitful collaboration was with Hudson and their trio of sex comedies were highlights of the ’60s, and perhaps represent the final gasp of old-school Hollywood before the dissolution of the Hays Code and the rise of ’70s New Hollywood. And let’s not forget dear Tony Randall, who plays a supporting part in all three of those movies.
Adam's Rib (1949) : 100%
Desk Set (1957) : 100%
Woman of the Year (1942) : 92%
Pat and Mike (1952) : 90%
The Sea of Grass (1947) : 17%
Guess Who's Coming to Dinner (1967) : 69%
Though Hepburn had already made two films with Tracy (Desk Set and Adam’s Rib, both 100%), she didn’t start an affair with her married co-star until filming their third: Woman of the Year. They maintained their relationship up until his death, while making three more films together. None would reach the Tomatometer heights of their pre-affair output, though Guess Who’s Coming to Dinner is a watershed moment in socially conscious filmmaking.
Joe Versus the Volcano (1990) : 62%
Sleepless in Seattle (1993) : 71%
You've Got Mail (1998) : 69%
America’s sweethearts for the ’90s. Even for a bit of the ’80s when you include Joe Versus the Volcano. But that movie was weird and nobody saw it, so the wistful Sleepless in Seattle is where most people’s affair with Hanks and Ryan started, as audiences turned out to the tune of a $220 million box office. A mere five years later, which felt like a lifetime back then, they were reunited for the adorably light You’ve Got Mail.
(Photo by Sabrina Lantos / © Lionsgate / courtesy Everett Collection)
Adventureland (2009) : 88%
American Ultra (2015) : 43%
Café Society (2016) : 70%
Eisenberg and Stewart are like two sides of the same coin: serious indie actors who occasionally get swept up in mass audience-friendly blockbusters. The two got paired in the Greg Mottola’s post-Superbad, joint Adventureland, and were cast in the critical and financial flop American Ultra. The two movies put Eisenberg and Stewart in some unflattering clothes (grody flannel and theme-park uniforms), so they traded up to dapper dresses and sharp suits with Woody Allen’s 1930s-set Cafe Society.
(Photo by Summit Releasing/courtesy Everett Collection)
Crazy, Stupid, Love. (2011) : 78%
Gangster Squad (2013) : 32%
La La Land (2016) : 92%
In terms of sheer star wattage, Gosling and Stone are definitely the ones people think of today when talking actors who played lovers multiple times. They were part of the romantic feast in Crazy, Stupid, Love. and were a bright spot in the cartoonishly awful Gangster Squad. But it was the classical La La Land that solidified these two as this generation’s Bogie and Bacall, Astaire and Rogers, etc.
(Photo by Weinstein Company/courtesy Everett Collection)
Jamon Jamon (1992) : 64%
Vicky Cristina Barcelona (2008) : 81%
Loving Pablo (2017) : 29%
From the early ’90s to a movie released just last month, Bardem and Cruz represent the longest span for on-screen coupling on this list, and there is little sign it’ll slow down considering the two are married in real life. Spanish-language Jamon Jamon was crucial in getting the two international attention, but the two wouldn’t reunite until Woody Allen’s sizzling Vicky Cristina Barcelona. In Loving Pablo, Cruz plays a journalist who falls in love with Escobar, though the movie is severely Rotten and tanked their average Tomatometer.
Down by Law (1986) : 90%
Johnny Stecchino (1991) : 46%
The Monster (1994) : 40%
Life Is Beautiful (1997) : 80%
The Tiger and the Snow (2005) : 21%
Most will have only seen Benigni and Braschi as the husband and wife in Life Is Beautiful, though they’ve been playing each other’s romantic interests for decades. It all started with Jim Jarmusch’s unconventional jailbreak film, Down by Law, with Braschi showing up in the second-half to host the escaped convicts, including Benigni. Two comedies, Monster and Johnny, were mostly ignored in America. They stuck it out to the Oscar-winning Life Is Beautiful.
Eyes Wide Shut (1999) : 74%
Days of Thunder (1990) : 38%
Far and Away (1992) : 48%
Cruise and Kidman were the celebrity couple of the ’90s, though they didn’t do their best work together. Days of Thunder and Far and Away are both Rotten, and they even dragged down poor Stanley Kubrick with Eyes Wide Shut, which has the lowest Tomatometer of the legendary filmmaker’s career.
(Photo by 20th Century Fox Film Corp. All rights reserved.)
The Cotton Club (1984) : 73%
Unfaithful (2002) : 50%
Nights in Rodanthe (2008) : 30%
Not Julia Roberts! (They only did two with Pretty Woman and Runaway Bride and our rule is three films minimum.) Gere and Lane’s relationship on-screen feels like the real thing played over a long period of time: first as young, electric lovers in Cotton Club; then trapped in marriage with Unfaithful; before settling into deep comfort with Nights in Rodanthe.
(Photo by Suzanne Tenner/TM and copyright ©20th Century Fox Film Corp. All rights reserved/courtesy Everett Collection)
Date Night (2010) : 67%
Oz the Great and Powerful (2013) : 59%
Third Person (2013) : 24%
One of the more unexpected repeated pairings, considering Franco rejects Kunis’ advances in Oz and Third Person being a little-seen flop. Their most memorable work together came in Date Night, playing seedy trash in love who add to the chaos of Steve Carell and Tina Fey’s romantic outing gone wrong.
(Photo by 20th Century Fox. All rights reserved/courtesy Everett Collection)
Cleopatra (1963) : 56%
The Sandpiper (1965) : 10%
Who's Afraid of Virginia Woolf? (1966) : 95%
The Taming of the Shrew (1967) : 86%
Doctor Faustus (1967) : 10%
The Comedians (1967) : 27%
Boom! (1968) : 8%
Hammersmith Is Out (1972) : 40%
There was much Hollywood glamor whenever Burton and Taylor were involved, though that didn’t exactly translate to many classics. The thriller Boom! is the worst-reviewed movie among everything featured in this entire list at 8%, and even their most famous epic, Cleopatra, isn’t Fresh on the Tomatometer. Who’s Afraid of Virginia Woolf? is a classic, though, and was nominated in every Oscar category in which it was eligible.
(Photo by New Line Cinema/ Courtesy: Everett Collection.)
The Wedding Singer (1998) : 68%
50 First Dates (2004) : 44%
Blended (2014) : 14%
Wedding Singer was the first movie to demonstrate Sandler had some dramatic chops, and remains one of the few Fresh highlights in his filmography. (Barrymore, of course, has had plenty of her movies go Certified Fresh.) They made two more movies with diminishing results, before Sandler left for permanent residence at Netflix.
(Photo by Jeffrey Reed/©Open Road Films/Courtesy Everett Collection)
When in Rome (2010) : 16%
Hit & Run (2012) : 49%
CHIPS (2017) : 17%
A cute couple in real life, but can y’all tone it down for the camera? Shepard plays one of many enchanted suitors in Rome so that just makes the cut, and afterwards turned to directing and starring in Rotten action-comedies: Hit and Run and the CHIPS remake, with Bell playing the girlfriend and wife, respectively.
