10 Films to Watch if You Like Sleepless in Seattle

Love is in the air and Cinema Paradiso has pieced together a special Valentine path from variations on a classic romance that continue to delight audiences of all ages. One good film leads to another, so why not discover some tips on what to watch next if you liked Nora Ephron's Sleepless in Seattle (1993) ?

A still from Sleepless in Seattle (1993)
A still from Sleepless in Seattle (1993)

The road to true love has never run smoothly and no one knows this better than the star-crossed couples in films linked by a rendezvous at the Empire State Building. Leo McCarey visited the story in An Affair to Remember (1957), with Cary Grant and Deborah Kerr being buffeted by fate and it's this film that helps Meg Ryan and Tom Hanks forge a long-distance connection in Nora Ephron's Sleepless in Seattle. These films remain irresistible in their own distinctive ways and lead on to some other tempting titles for Cinema Paradiso users to enjoy.

Sleepless in Seattle

Directed by Nora Ephron, Sleepless in Seattle isn't a remake of An Affair to Remember. But it would be lost without its most iconic scene and its innate sense of romance. One conversation proves the point. As Annie Reed (Meg Ryan) and best friend Becky (Rosie O'Donnell) are watching the 1957 weepie, Annie declares that this was a time when people really knew how to be in love. 'That's your problem,' Becky replies, 'You don't want to be in love. You want to be in love in a movie.'

The project had been in the works for some time before Ephron became involved. Virginia schoolteacher Jeff Arch had written the original draft after the birth of his son. Producer Gary Foster had been suitably touched by the story about a Baltimore woman being charmed by a Seattle widower's appearance on a late-night radio phone-in and he had given it to David S. Ward (who had won an Oscar for George Roy Hill's con classic, The Sting, 1973) to rework, while he set about finding co-stars who would melt hearts.

Initially, Meg Ryan and then-husband Dennis Quaid were linked with the roles. But Julia Roberts, Kim Basinger, Demi Moore and Madonna all expressed an interest after Foster passed the screenplay to Ephron for a little polishing in conjunction with her writer sister, Delia. The pair were no strangers to writing for the screen, as parents Henry and Phoebe Ephron had worked on such classics as Jean Negulesco's Daddy Long Legs (1955) and Walter Lang's Carousel (1956) and Desk Set (1957). Indeed, Phoebe was so well known around the film colony that when she had taken the teenage Nora to watch An Affair to Remember and she had sobbed all the way through it, her mother had introduced her to Cary Grant to help her feel better.

Ephron had already secured a couple of Oscar nominations of her own for Mike Nichols's Silkwood (1985) and Carl Reiner's When Harry Met Sally... (1989). But her directorial career had gotten off to a disappointing start after the critics had turned on her Julie Kavner comedy, This Is My Life (1992). Undaunted, Ephron was convinced she could do something special with Sleepless in Seattle and her confidence was further boosted when she convinced Tom Hanks to take the role of Sam Baldwin after he had complained that his son, Jonah, got more laughs than he did.

Among the conditions that Hanks stipulated in agreeing to reunite with Ryan after John Patrick Shanley's Joe Versus the Volcano (1990) was a chance to rewrite some of his dialogue and the opportunity to improvise on the set. One of the scenes that emerged from this off-the-cuff byplay saw Sam and brother-in-law Greg (Victor Gerber) joke about getting emotional while watching Robert Aldrich's macho war adventure, The Dirty Dozen (1967). But shooting didn't always go so smoothly, as Nathan Watt (who had beaten Jason Schwartzman to the role of Jonah) was so starstruck by Hanks that he kept winding him up and had to be replaced. Hanks has since admitted to having been cranky during the first phase of production and was mightily relieved when Ross Malinger was cast as his replacement eight year-old son.

More problems arose when Foster was denied permission to shoot at the Empire State Building. As owner Leona Helmsley - the flamboyant businesswoman who was nicknamed 'the Queen of Mean' - was behind bars at the time for tax evasion, Ephron asked the publicist friend who represented Helmsley to pay her a visit in prison and she agreed to let them use the lobby and the observation deck for six hours. This didn't leave them long enough to shoot Valentine's Day meeting and the scene had to be filmed in Seattle, where Ephron called in a favour from another old friend to shoot in a hangar at a naval base that was about to be decommissioned. When the USN declined her request, Ephron asked Elizabeth Taylor's ex-husband, Senator John Warner, to use his influence as a former Secretary of the Navy and, as was often the case, she ended up getting her way.

She also struck lucky in securing the services of Swedish cinematographer, Sven Nykvist, who had won Academy Awards for his work on Ingmar Bergman's Cries and Whispers (1973) and Fanny and Alexander (1982) and who had shown a keen eye for urban America in Woody Allen's Crimes and Misdemeanors (1989). Of the many striking images that Nykvist created, the most memorable is the first, as the camera rises above the Chicago cemetery in homage to Saul Steinberg's famous illustration, 'View of the World From 9th Avenue', which had adorned the cover of The New Yorker in March 1976.

The soundtrack was also a triumph, although Ephron's insistence on finding room for 20 songs caused composer John Barry to quit. He was replaced by Marc Shaiman, who shared an Oscar nomination with Ramsey McLean for the Harry Connick, Jr. number, 'A Wink and a Smile'. But the standouts for many will be Nat King Cole's rendition of 'Stardust', Louis Armstrong's 'A Kiss to Build a Dream On' and a pair of Jimmy Durante gems, 'Make Someone Happy' and 'As Time Goes By', which had been performed so memorably by Dooley Wilson in Michael Curtiz's Casablanca (1942).

A still from Julie and Julia (2009) With Amy Adams
A still from Julie and Julia (2009) With Amy Adams

Earning $126 million at the US box office alone on a budget of $22 million, the picture was the runaway romantic hit of 1993. On the back of its success, Ephron (who had also taken a vocal cameo as 'Disappointed in Denver') coaxed Hanks and Ryan into teaming for a third and last time on You've Got Mail (1998), a digital media reworking of another venerated classic, Ernst Lubitsch's The Shop Around the Corner (1940). She also made amends to Parker Posey for cutting her part in Sleepless in Seattle by casting her as Hanks's publishing executive girlfriend. These collaborations would be the highlights of a career that also included scripting credits on Mike Nichols's Heartburn (1986) and Herbert Ross's My Blue Heaven (1990) and writer-directing gigs on Mixed Nuts (1994), Michael (1996), Bewitched (2005) and Julie and Julia (2009).

  • An Affair to Remember (1957)

    Play trailer
    1h 49min
    Play trailer
    1h 49min

    It's comparatively very rare for a director to remake their own film. Given the vast number of titles in our library, it's not surprising that Cinema Paradiso can offer users the chance to see some of the choicest examples. Indeed, some of the biggest names in screen history have indulged in a little rebooting, including Frank Capra (Lady For a Day, 1933 & Pocketful of Miracles, 1961) and Alfred Hitchcock (The Man Who Knew Too Much, 1934/1956).

    An Affair to Remember saw Leo McCarey team Deborah Kerr and Cary Grant in the roles of playboy painter Nickie Ferrante and aspiring Boston singer Terry McKay. Initially, there was talk of Ingrid Bergman playing Terry, although she would eventually reunite with Grant on Stanley Donen't chic romcom, Indiscreet (1958), which also includes a meeting after a lengthy separation. Doris Day was also linked with the project alongside Howard Keel and it would have been intriguing to see her perform the nightclub songs that were dubbed by Marni Nixon, who had also provided Kerr's singing voice in Walter Lang's The King and I (1956).

    Amusingly, during their first conversation, Grant tells Kerr that he is a cat burglar, which exactly the role that he had played opposite Grace Kelly in Hitchcock's To Catch a Thief (1955). But the encounter must have evoked memories for the 53 year-old, as he had met third wife Betsy Drake on an ocean voyage and she spent much of the production trying to help Grant kick his 60-a-day smoking habit.

    Grant and Kerr brought an air of British sophistication to roles that felt all the more natural as McCarey encouraged them to improvise as much as they wished. However, he also slipped them a few lines from his own back catalogue, as Kerr's speech about going their separate ways down alternatively straight and twisting paths echoed Irene Dunne's words and hand gestures in a scene with Grant in The Awful Truth (1937).

    Despite playing Grant's grandmother in the film, Cathleen Nesbitt was only 15 years older than him. Curiously, An Affair to Remember failed to receive a single Oscar nomination, although it has since been voted the fifth greatest screen romance by the American Film Institute.

  • King Kong (1933)

    1h 36min
    1h 36min

    Completed in 1901, the Empire State Building has featured in dozens of films over the last 120 years. It was fetishised by Andy Warhol in the 24-hour silent, Empire (1964), obliterated by aliens in Roland Emmerich's Independence Day (1996) and used as a portal to Mount Olympus via an elevator to the 600th floor in Chris Columbus's Percy Jackson & The Lightning Thief (2010). But its most iconic appearance sees it being climbed by the giant ape in Ernest B. Schoedsack and Merian C. Cooper's groundbreaking 'beauty and the beast' saga. The sight of bi-planes buzzing Willis O'Brien's stop-motion creation, as he tries to abscond with Fay Wray, was inspired by Cooper hearing a plane flying overhead as he left his office in downtown Manhattan and realising that a scene involving these contrasting wonders of the world could highlight the dangers posed by modern weapons.

  • The Awful Truth (1937)

    1h 27min
    1h 27min

    Stars from the first two versions of Love Affair were teamed by Leo McCarey in this screwball classic, which was adapted from a 1923 play by Arthur Richman. But rather than playing lovers who are kept apart by fate, Irene Dunne and Cary Grant play a well-heeled married couple, Lucy and Jerry Warriner, who can't make their divorce work, as they keep attracting ghastly suitors who make them realise how much better off they are together. How Tay Garnett must have rued claiming the script was 'about as funny as the seven-year-itch in an iron lung', as McCarey went on to win the Oscar for Best Director. Ralph Bellamy was also nominated for a droll display as a momma's boy oil tycoon that included a magnificently tin-eared rendition of 'Home on the Range'. Ironically, when Grant and Dunne reunited on My Favourite Wife (1940), Garson Kanin had to replace McCarey because he had injured his back in a car crash.

    Director:
    Leo McCarey
    Cast:
    Irene Dunne, Cary Grant, Ralph Bellamy
    Genre:
    Comedy, Classics, Romance
    Formats:
  • The Philadelphia Story (1940)

    Play trailer
    1h 48min
    Play trailer
    1h 48min

    Bill Pullman was apparently disappointed that the allergy-afflicted Walter didn't feature more prominently in Sleepless in Seattle. He had been informed that he would be more akin to Mike Connor, the shutterbug in George Cukor's Best Picture-winning adaptation of Philip Barry's Broadway hit, who finds himself competing for the attentions at a swish society wedding of bride-to-be Tracy Lord (Katharine Hepburn) with her debonair ex-husband, CK Dexter Haven (Cary Grant). As Stewart had won the Oscar for Best Actor, Pullman's frustration at Walter morphing into a stooging support can be understood. But Hollywood had already had a serviceable variation on this particular ménage, as Frank Sinatra and Bing Crosby had vied for heiress Grace Kelly in Charles Walters's swinging musicalisation, High Society (1956). Pullman would fare better in another classic romcom, however, as the brother of the coma victim to whom subway worker Sandra Bullock claims to be engaged in Jon Turteltaub's While You Were Sleeping (1995).

  • On the Town (1949)

    Play trailer
    1h 34min
    Play trailer
    1h 34min

    It's back to the Empire State for Gene Kelly and Stanley Donen's radical reworking of a 1944 Betty Comden and Adolph Green stage show that had been scored by Leonard Bernstein. Not content with reshaping the scenario and ditching most of the original songs, Kelly and Donen also decided to shoot on the streets of New York to capture the energy of the city, as three sailors spend a 24-hour furlough looking for love. But, while Frank Sinatra and Jules Munshin manage to hook up with cabby Betty Garrett and anthropologist Ann Miller, Kelly seems set to fail in his bid to track down subway pin-up, Miss Turnstiles (Vera-Ellen), before rendezvousing with his shipmates atop what was then the Big Apple's highest landmark. Musical director Roger Edens deserves huge credit for reshaping the songbook, but it's the innovative direction that transformed a show MGM chief Louis B. Mayer had branded 'smutty' and 'Communistic' into a thrilling city symphonic time capsule.

  • Grass Is Greener (1960)

    Play trailer
    1h 44min
    Play trailer
    1h 44min

    Cary Grant and Deborah Kerr found themselves in dire financial straits as the Earl and Countess of Rhyall in Stanley Donen's adaptation of a West End play by Hugh Williams and Margaret Vyner, the acting-writing partnership. Donen had originally hoped to cast Rex Harrison and wife Kay Kendall as Victor and Hilary, but they had been forced to withdraw shortly before Kendall succumbed to leukaemia at the age of 33. Grant agreed to switch from the part of American interloper Charles Delacro, who was played by Robert Mitchum, in the third of his four pairings with Kerr and the last of his trio with Jean Simmons, who essays Victor's old flame. Contrasting Anglo-American fortunes in the postwar world, this satire on the enduring relevance of noblesse oblige captures a Britain about to disappear as the Sixties started to swing.

  • Heaven Can Wait (1978)

    Play trailer
    1h 37min
    Play trailer
    1h 37min

    The sharp-eyed will have spotted a clip from Warren Beatty's cinematic past in Love Affair, as the footage used in a television commercial was gleaned from this self-directed romantic fantasy, which reworked the storyline of Alexander Hall's supernatural charmer, Here Comes Mr Jordan (1941). American Football provides the link between the Beatty projects, although things would have been different if he had persuaded Muhammad Ali to play Joe Pendleton as a boxer being returned to Earth after a celestial slip of the pen had called him too soon. Beatty had played quarterback at high school and the sporting action is laudably authentic. However, the focus falls on his relationships with his heavenly mediator (James Mason, after Cary Grant had refused to come out of retirement) and with environmental activist Betty Logan, who was played by Julie Christie, even though she had split from Beatty since their earlier teamings on Robert Altman's McCabe & Mrs Miller (1971) and Hal Ashby's Shampoo (1975).

  • Crimes and Misdemeanors (1989)

    Play trailer
    1h 40min
    Play trailer
    1h 40min

    Having worked with Woody Allen on Another Woman (1988) and the 'Oedipus Wrecks' segment of New York Stories (1989), Swedish cinematographer Sven Nykvist returned Stateside for a picture that deeply impressed Nora Ephron. Allen had written the screenplay during a European vacation after becoming convinced that he had been too soft on the characters in Hannah and Her Sisters (1986). Among the considered titles were The Sight of God and Windows on the Soul, but Allen plumped for Crimes and Misdemeanors as it reinforced the influence of Fedor Dostoevsky's Crime and Punishment on the fate of ophthalmologist Martin Landau after mistress Anjelica Huston threatens to expose that he is not an upstanding member of the community. Initially, Allen had not intended to write a role for himself, but the studio insisted and he created an insecure documentary maker who is forever clashing with a pompous TV producer, whom Alan Alda based on his M*A*S*H (1972-82) colleague, Larry Gelbart.

  • You've Got Mail (1998)

    1h 55min
    1h 55min

    By the time Nora Ephron came across Hungarian Miklós László's 1936 play, Parfumerie, it had been providing inspiration for over six decades. It had provided the basis for two musicals, Robert Z. Leonard's Judy Garland vehicle, In the Good Old Summertime (1949), and the 1963 Broadway show, She Love Me, which was written by Jerry Bock and Sheldon Harnick of Fiddler on the Roof (1971) fame. Even though she didn't own a computer at the time, Meg Ryan signed up alongside Tom Hanks to play a Manhattan children's bookshop owner who has no idea that her online penpal works for the soulless corporation that is trying to destroy her business. Michael Palin spent a week shooting scenes as an author with designs on Ryan, who was based on Thomas Pynchon, but the footage was left on the cutting-room floor.

    Director:
    Nora Ephron
    Cast:
    Tom Hanks, Elwood Edwards, Meg Ryan
    Genre:
    Drama, Comedy, Romance
    Formats:
  • Date Movie (2006)

    1h 21min
    1h 21min

    A couple of passing jokes about the Empire State Building is all that links this scattershot spoof to the Affair/Sleepless universe. But director Aaron Seltzer and co-scenarist Jason Friedberg deserve credit for packing so many romcoms into an 81-minute picture. We can't pretend their efforts are always riotously funny and viewers are often more likely to groan at the quality of the gags than chuckle. But it's fun recognising references to the likes of When Harry Met Sally..., Joel Zwick's My Big Fat Greek Wedding (2002) and Jay Roach's Meet the Fockers (2004) to name but three. Always the trouper, Alyson Hannigan gives her all from deep inside a large fat suit and several layers of latex as the waitress at a family restaurant who seeks the advice of dating counselor Tony Cox to help her win the heart of dreamboat customer, Adam Campbell. There are around 50 films lampooned here. See how many you can spot.

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