05/22/2014 09:19 am ET Updated May 22, 2014

Can Repeat Rom-Com Couples Find Love Again And Again?


Sometimes Hollywood romance strikes twice -- or three, four and five times. Serial romantic-comedy couples can tell you that more than anyone else. For some, their numerous collaborations led to continued success. Others learned that love doesn't always hold up on second thought. Adam Sandler and Drew Barrymore are giving it a third go this weekend with "Blended." Early reviews are bad, and the box-office fate is yet to be seen (it opens against "X-Men: Days of Future Past"), but here's a look at a handful of rom-com soul mates who've tried to win our hearts multiple times. (Note: All box-office grosses listed have been adjusted for inflation.)

  • Diane Keaton and Woody Allen
    <strong>"Play It Again, Sam" (1972): </strong>Woody Allen almost passed Keaton over for this "Casablanca" sendup because she
    United Artists
    "Play It Again, Sam" (1972): Woody Allen almost passed Keaton over for this "Casablanca" sendup because she was too tall. Had he, one of the most iconic film collaborations may never have happened. "Play It Again, Sam" premiered to magnanimous reviews and ignited a pairing that's seen enduring success.
    Box office: N/A

    "Sleeper" (1973): Keaton's follow-up to "Play It Again, Sam" was this sci-fi parody about a health-food store owner who's cryogenically frozen and reawakened 200 years later. Again, Keaton and Allen were met with praise from all corners. The movie has 100 percent positive reviews on Rotten Tomatoes.
    Box office: $97.9 million

    "Love and Death" (1975): This satire about two Russians in the Napoleonic era marks Allen's transition between "Sleeper" and "Annie Hall." It, too, earned high praise and a significant box-office tally. "Besides being one of Woody's most consistently witty films, 'Love and Death' marks a couple of other advances for Mr. Allen as a film maker and for Miss Keaton as a wickedly funny comedienne," wrote New York Times critic Vincent Canby.
    Box office: $88.7 million

    "Annie Hall" (1977): Allen and Keaton's dynamic only proliferated as the '70s concluded, and with "Annie Hall" the duo became Oscar winners (Allen, Best Director; Keaton, Best Actress). The movie itself stole Best Picture from the first "Star Wars" installment, and AFI ranks it the 11th greatest film of passion. Allen was surprised that it emerged as his signature movie, but critics called it "touching" and "clever."
    Box office: $149.6 million

    "Manhattan" (1979): Say what you will about what light the cross-generational romance in "Manhattan" shines on Allen's current controversies, but the Oscar-nominated romance was met with universal praise. Unsurprisingly, there's no traditional happy ending for this dramedy, but that didn't damage the duo's esteem among moviegoers or the movie's box-office prosperity.
    Box office: $130.4 million
  • Julia Roberts and Richard Gere
    <strong>"Pretty Woman" (1990):</strong> One of the highest-grossing romantic comedies of all time, "Pretty Woman" made Julia
    "Pretty Woman" (1990): One of the highest-grossing romantic comedies of all time, "Pretty Woman" made Julia Roberts Hollywood's most bankable actresses -- an unexpected prospect for a movie that opened to divisive reviews. It's obviously Roberts' charm that carries the movie, rather than the sexism claims some critics hurled at it. (We defended the film earlier this year when it was snubbed from a list of the best rom-coms since "When Harry Met Sally...") But naysayers be damned, because "Pretty Woman" earned Roberts her second Oscar nomination, and moviegoers swooned at her on-screen coupling with Richard Gere.
    Box office: $323.6 million

    "Runaway Bride" (1999): Gere and Roberts reunited with director Garry Marshall for this "Pretty Woman" wannabe, but the duo's charm was bankrupted by a weak story. "The difference between 'Pretty Woman' and 'Runaway Bride' is that we can no longer buy Roberts in her tearful romantic-melancholy mode," Entertainment Weekly's Owen Gleiberman wrote. Audiences did buy it, though, as the movie was the ninth highest-grossing of 1999. Perhaps it was the middling reviews that killed Roberts and Gere's rom-com dominance. The next time we'd see Roberts on the big screen (in "Erin Brockovich"), she'd be a new person. The pair hasn't starred together again since.
    Box office: $216.7 million
  • Kate Hudson and Matthew McConaughey
    <strong>"How to Lose a Guy in 10 Days" (2003):</strong> Critics labeled it "<a href="http://www.variety.com/review/VE11179197
    Warner Bros.
    "How to Lose a Guy in 10 Days" (2003): Critics labeled it "ill-conceived," "too light on laughs" and "an opportunity wasted." The reviews especially stung because "How to Lose a Guy" is basically a Shakespearean scheme for the 21st century. Still, enough were taken with Hudson and McConaughey's chemistry to make the movie a sizable success.
    Box office: $136.6

    "Fool's Gold" (2008): Andy Tennant ("Sweet Home Alabama," "Hitch") decided it would be a good idea to reunite McConaughey and Hudson for a movie about a divorced couple who spark another flame while hunting down lost treasure. Surely he couldn't have expected much critical acclaim to come of it, right? None did. "Fool's Gold" was one of the worst-reviewed films of 2008. "It could have been called 'How to Lose an Audience in 10 Minutes,'" The Hollywood Reporter's Michael Rechtshaffen wrote. The movie was bankable enough, but it took in only half of what "How to Lose a Guy in 10 Days" made. Hudson and McConaughey have barely made a dent in their path to claim the same territory that Ryan and Hanks did 20 years before them.
    Box office: $77.3 million
  • Katharine Hepburn and Cary Grant
    <strong>"Sylvia Scarlett" (1935):</strong> Hollywood studio system politics aside, it's hard to believe Hepburn and Grant wen
    "Sylvia Scarlett" (1935): Hollywood studio system politics aside, it's hard to believe Hepburn and Grant went on to make three more films together based on the reception "Sylvia Scarlett" saw. It couldn't recoup its $641,000 budget at the box office, and critics weren't taken with the movie's progressive sexual politics or Grant's Cockney accent.
    Box office: $8.6 million

    "Bringing Up Baby" (February 1938): Again, Hepburn and Grant are representations of how dramatically the Hollywood development process has shifted. Initial reception for "Bringing Up Baby" was mixed, and the movie was considered a flop until it was re-released in the '40s. It didn't hit its peak acclaim until it began to air on TV in the '50s, at which point film critics confirmed its quality. Today, it's often referred to as one of the greatest movies of all time.
    Box office: $18.7 million

    "Holiday" (June 1938): By the time this screwball comedy opened, Hepburn was labeled "box-office poison." "Holiday" was well-liked, but it was by no means labeled a financial victory.
    Box office: N/A

    "The Philadelphia Story" (1940): In a pattern that's antithetical to today's Hollywood business model, three semi-flops gave way to yet another Hepburn-Grant assembly. But this time, it worked. "The Philadelphia Story" was beloved upon its release and proved to be turnaround for Hepburn's bankability. Both stars received Oscar nominations and then never again appeared in a movie together.
    Box office: $55 million
  • Meg Ryan and Tom Hanks
    <strong>"Joe Versus the Volcano" (1990):</strong> Ryan and Hanks may be the most emblematic romantic-comedy couple of the las
    Warner Bros.
    "Joe Versus the Volcano" (1990): Ryan and Hanks may be the most emblematic romantic-comedy couple of the last 40 years, but it isn't thanks to this John Patrick Shanley-directed love story. Roger Ebert loved "Volcano," but most critics were lukewarm, and the movie ultimately fizzled out with $39 million in grosses.
    Box office: $71.5 million

    "Sleepless in Seattle" (1993): Then along came Nora Ephron, and all was right with the world. "Sleepless in Seattle" earned Ephron and co-writers David S. Ward and Jeff Arch an Oscar nod for Best Original Screenplay, and today the off-kilter, love-at-first-listen romance remains a channel-surfing classic. "Ms. Ephron and her associates create a make-believe world so engaging that 'Sleepless in Seattle' is finally impossible to resist," Vincent Canby wrote in his New York Times review.
    Box office: $207.8 million

    "You've Got Mail" (1998): As if Mindy Kaling's endorsement weren't enough to enunciate the Ryan-Hanks impact, two Vulture writers battled it out last year to determine whether "Sleepless in Seattle" or "You've Got Mail" was the superior love story. No self-respecting rom-com fan can abstain from that great debate of the 1990s. "You've Got Mail" has its serious detractors, like The Washington Post's Michael O'Sullivan, who wrote, "This film made me feel like a Christmas goose being fattened for slaughter. Its force-fed diet of whimsy cloyed long before the eagerly anticipated romantic payoff arrived to put me out of my misery." Despite its hammy imperfections, magic did strike twice -- "You've Got Mail" is another '90s rom-com fave and an essential entry in the Nora Ephron cannon.
    Box office: $168.5 million

  • Drew Barrymore and Adam Sandler
    <strong>"The Wedding Singer" (1998):</strong> No one used the word "original" to describe this movie, but it prospered anyway
    Columbia Pictures
    "The Wedding Singer" (1998): No one used the word "original" to describe this movie, but it prospered anyway, in large part thanks to Barrymore and Sandler's likability. At the '90s rom-com apex, "The Wedding Singer" was a box office standout and the perfect fodder for endless TV airings.
    Box office: $116.7

    "50 First Dates" (2004): In "50 First Dates" lies the epitomization of repeat romance gone wrong: There's no denying Barrymore and Sandler's chemistry in the amnesia-plotted comedy, but the crude script (by "Tommy Boy" and "Anger Management" scribe Peter Segal) distracts from the pair's potential. Some critics still praised the film, but many agreed with Claudia Puig's sentiments: "'50 First Dates' is working awfully hard to be romantic and not hard enough to be a comedy." Nonetheless, audiences flocked to the film in a way they didn't to the second comings of Gere/Roberts and Hudson/McConaughey.
    Box office: $151.7 million

Chime in below on your favorite rom-com pairs and whether you think the aforementioned couples made multiple love stories for the ages.



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