This month will see the release of Destination Wedding, a new romantic comedy starring Keanu Reeves and Winona Ryder. The film marks the third occasion they have appeared on-screen as a couple, having previously played doomed lovers in Francis Ford Coppola’s lush horror epic Bram Stoker’s Dracula and Richard Linklater’s hallucinatory science-fiction thriller A Scanner Darkly (the pair also appeared in The Private Lives of Pippa Lee together but not at the same time).

Their reunion fits into a broad tradition of actors portraying couples in unrelated films. It’s one that is still prevalent today, as seen in the oft-repeated pairings of Adam Sandler and Drew Barrymore, Jamie Foxx and Kerry Washington, Casey Affleck and Rooney Mara, Jesse Eisenberg and Kristen Stewart, Bradley Cooper and Jennifer Lawrence, and of course, Emma Stone and Ryan Gosling.

While there are far too many cases of cross-movie couplings to record at all once, here are a few examples throughout the decades that have proven especially memorable:

Robert Mitchum and Jane Russell

His Kind of Woman (1951) and Macao (1952)

Photograph: Allstar Picture Library

The “star system” engendered by Hollywood studios between the 1930s and the 1960s produced some of the most iconic on-screen (and off-screen) duos of all time, including Ginger Rogers and Fred Astaire (who made a total of 10 movies together), Katharine Hepburn and Spencer Tracy (nine), Humphrey Bogart and Lauren Bacall (four), and Rock Hudson and Doris Day (three). But in terms of pure heat, no returning screen lovers can compete with the sly, hulking Mitchum and the smoldering, voluptuous Russell in these back-to-back port-side noirs. The pair emitted pure electricity for every moment they shared the screen, and it’s a shame we only got two outings from them.

Elizabeth Taylor and Montgomery Clift

A Place in the Sun (1951), Raintree County (1957) and Suddenly Last Summer (1959)

Elizabeth Taylor and Richard Burton

Cleopatra (1963) and Who’s Afraid of Virginia Woolf? (1966)

Photograph: various

Rumored to have been romantically involved throughout their time together, it’s now widely believed that Taylor was acting as a beard for the allegedly closeted Clift. Regardless of the true nature of their relationship, the two were very close, and that closeness is tangible throughout the trio of psychological melodramas they made together. Serving as bookends, the achingly fatalistic A Place in the Sun and the feverishly psychosexual Suddenly Last Summer reflect the various physical and emotional traumas that beset Clift during his life, for which Taylor often bore close personal witness.

Taylor would likewise go on to make 11 movies with her future (two-time) husband Richard Burton, including standouts Cleopatra, one of the biggest studio bombs of all time, and Who’s Afraid of Virginia Woolf? (released the same year Clift suffered his fatal heart attack), for which they each turned in career-best performances (earning Taylor her second Oscar).

Woody Allen and Diane Keaton

Play It Again Sam (1972), Sleeper (1973), Love and Death (1975), Annie Hall (1977), Manhattan (1979) and Manhattan Murder Mystery (1993)

Photograph: Allstar Picture Library

From Allen’s early slapstick comedies to his groundbreaking transitional films, this physically mismatched pair updated the madcap genius of classic screwballs, imbuing it with a sharp sense of existentialist irony, and creating in the process one of the all-time iconic movie couples in Annie Hall. Unfortunately, their half-hearted attempt at recapturing the magic with 1993’s Manhattan Murder Mystery (based on a subplot cut from an early version of Hall) falls totally flat.

The less said about Allen’s fraught collaborations with future partner Mia Farrow throughout the 80s and early 90s, the better.

Michael Douglas and Kathleen Turner



Romancing the Stone (1984), Jewel of the Nile (1985), The War of the Roses (1989)

Photograph: Allstar Picture Library

The popular pairing of an emergent Michael Douglas and a height-of-her-powers Kathleen Turner is actually more of a love triangle, thanks to the equally important contribution of DeVito (he co-starred in all three movies and directed the third). The first entry, from director Robert Zemeckis, was the epitome of slick, high-energy 80s entertainment, although as with most cases of rushed sequels, Jewel of the Nile proved a slightly disappointing follow-up. But that only makes the conclusion of the trifecta, The War of the Roses, all the more fascinating for its subversion of audience expectations. Rather than a comedy about opposites attracting, it’s an ever-escalating battle of attrition between two toxic monsters on the path towards mutually assured destruction.

Meg Ryan and Tom Hanks

Joe vs the Volcano (1990), Sleepless in Seattle (1993), You’ve Got Mail (1998) and Ithaca (2015)

Composite: Rex

The romantic pairings of Ryan and Hanks are a study in peaks and valleys. While its reputation has steadily improved over the years, their first go-round in the absurdist comedy Joe vs the Volcano was met with savage reviews and poor box office. That failure would soon be forgotten, however, as their subsequent efforts – both written and directed by Nora Ephron – would go on to achieve massive success.

While Sleepless in Seattle has held on to its popular cachet, You’ve Got Mail is a little more circumspect these days, thanks to its dated premise (the nostalgia evoked by that swoosh noise is more cringe-worthy than joyful), as well as its truly baffling politics. If audiences were ever fully on board with Ryan’s character shacking up with the corporate yuppie that drove her out of business, they’re less so now, in a post-recession world. (This doesn’t even take into account the weird subplot about her best friend carrying a torch for fascist dictator Francisco Franco.) Still, these 90s offerings from Ryan and Hanks remain generally beloved, though clearly that wasn’t enough to bring audiences out for the duo’s brief 2015 reunion in Ryan’s lone directorial effort, Ithaca.

Julia Roberts and Richard Gere

Pretty Woman (1990) and Runaway Bride (1999)

Composite: Rex

If there’s any romcom couple of the last 40 years that can rival Ryan and Hanks, it’s Julia Roberts and Richard Gere, who opened the 90s big with Pretty Woman, a modern-day fairytale that hasn’t lost an ounce of its status in the intervening decades (despite its premise, which flies in the face of most modern sensibilities). Reteaming with director Gary Marshall, the team closed out the decade strongly nine years later with Runaway Bride, a movie that never came close to matching Pretty Woman in terms of cultural impact, but which did nevertheless prove a gigantic financial success.

Leonardo DiCaprio and Kate Winslet



Titanic (1997) and Revolutionary Road (2008)

Composite: Rex

Despite director James Cameron’s follow up of 12 years later, Avatar, dethroning it from the all-time top box office spot, Titanic still feels like the ultimate American blockbuster. At least a third of the credit for that has to go to DiCaprio and Winslet, who remain the avatars for all star-crossed lovers of the modern age (the rest of the credit must be divided between Cameron and his special effects team, and musical collaborators James Horner and Celine Dion).

Recognition should also be given to DiCaprio and Winslet for choosing an adaptation of Richard Yates’s notoriously acerbic and depressing domestic drama, Revolutionary Road, for their reunion a little over 10 years later. Their intentions don’t make the movie any less unwatchable, or their performances any less shrill, but still – props to them for trying something different.

Tom Cruise and Nicole Kidman



Days of Thunder (1990), Far and Away (1992) and Eyes Wide Shut (1999)

Composite: Rex

It’s fitting that Tom Cruise and Nicole Kidman – whose on-screen and off-screen romance helped shape 90s pop culture – should usher in the decade with two pieces of flashy, action-packed bombast, and close it out with an unsettling, slow-burn fugue about the anxieties of sexual fidelity and impotence. It was Cruise’s dream to work with director Stanley Kubrick, but the film’s grueling 15-month shoot was beyond anything he or Kidman anticipated.

Many in the press speculated that the production (as well as its disappointing reception) was a major factor in the dissolution of their marriage a little over a year later. While Kidman has stated this wasn’t the case, their last on-screen collaboration together – and Kubrick’s final film – remains a spooky harbinger of things to come, both in regard to Cruise and Kidman’s relationship, as well as middle-class America as a whole, floating as it did through the decade in an almost trance-like state, unsatisfied with what it had while choosing to ignore the inklings of danger lurking in from the edges.