Hollywoodland (2006)

A surprisingly spry biopic of actor George Reeves, whose unmeteoric career led to him playing Superman on TV (1952–58), and eventually to a suicide that might’ve been a murder. Ben Affleck, as Reeves, and Diane Lane, as Toni Mannix, a Hollywood producer’s wife and aging tramp, rise to the occasion, and the film is a bath in postwar semi-affluence. Ignore the Adrien Brody framing story if you can.

Far from Heaven (2002)

Frank and Cathy (Dennis Quaid and Julianne Moore) are the perfect 1950s couple: he’s a successful businessman; she’s a beautiful, impeccable hostess with a flawless home, two well-behaved children, and a loyal housekeeper. The facade cracks when Cathy catches Frank kissing another man—and then finds solace in the sympathetic companionship of her gardener, a courteous, intelligent man who happens to be black. This movie is an homage to the Douglas Sirk dramas of the 1950s, right down to the typeface over the opening credits and the swelling Elmer Bernstein score, and it’s a dead-serious “women’s film” melodrama. Gloved hands, cocktails before dinner, crinoline skirts, and the ubiquity of casual prejudice—director Todd Haynes’s film is almost a deliberate attempt to make the nervy movie about the failure of middle-class surfaces that audiences should’ve had the chance to see in 1956, but that the studios were too timid to make.

Diner (1982)

Film poster for Diner - Copyright 1982, MGM
Film poster for Diner – Copyright 1982, MGM (Photo credit: Wikipedia)

Barry Levinson’s debut film is a small masterpiece of social anthropology. Here he recreates the 1959 stuck-in-a-groove lifestyle of six Baltimore guys in their twenties, swapping yucks at the all-night eatery over gravied french fries, like they have since they were kids, and not being much more savvy than their childhood selves about adulthood or women. The semi-improvised banter is fascinating, and the clothes, norms, styles, lingo, and music are all on the money. Steve Guttenberg and Mickey Rourke shine as they did only here, Kevin Bacon and Daniel Stern have rarely had better roles, and Paul Reiser expertly energizes the ensemble with wisecracks. (The sixth guy, Tim Daly, is a relative dull straight man with dull girl problems.) Guttenberg’s slightly dull-witted Colts fanatic is getting married, and the guys collect in the midwinter, in their wool overcoats, to see if it’ll actually happen. If it sounds like a hundred other small movies from the 1980s on, you’re right—but this is the first of its kind, and it’s the best. (Incidentally, this movie also served as a significant “how to” lesson in chatty screenwriting for a young fanboy named Quentin Tarantino.)

American Graffiti (1973)

The year 1962 was still the 1950s in George Lucas’s small California burg, where, for some, Buddy Holly’s death marked the end of something grand, and the looming threat of the draft and Vietnam meant that something else entirely was on its way. How could the antiseptic overlord of the Star Wars industry have thunk up something so charming, spontaneous, idiosyncratic, and humane? A 1970s masterpiece, this film marks the beginning of an entire culture phenomenon: retro cool.

Rebel Without a Cause (1955)

Cropped screenshot of Natalie Wood and James D...
Cropped screenshot of Natalie Wood and James Dean in the trailer for the film Rebel Without a Cause (Photo credit: Wikipedia)

A key film, sprouting from the middle of the decade and masterfully drawing the battle lines for what would later become known as “the generation gap,” but more than that: Nicholas Ray’s temple-pounding James Dean saga doesn’t glamorize the 1950s; its milieu is lower-middle-class, and its social web is stretched to the tearing point. There may not be a clearer emotional portrait of mid-century America.

The Wild One (1953)

English: A photograph promoting the film The W...
English: A photograph promoting the film The Wild One depicts actor Marlon Brando. (Photo credit: Wikipedia)

Marlon Brando, in a leather jacket and on a motorcycle, scaring the bejeezus out of honest small-town folk with his lawless, devil-may-care youthfulness. The movie in which Brando, when asked what he’s rebelling against, merely answers “What’ve you got?”

Pirates of the Caribbean: Dead Man’s Chest (2006)

Pirates of the Caribbean: Dead Man's Chest
Pirates of the Caribbean: Dead Man’s Chest (Photo credit: Wikipedia)

Ripe blockbuster cheese, but one that packs in a cannibal tribe, a voodoo queen, a ship-consuming monster cephalopod, the Flying Dutchman, Davy Jones’s locker, Davy Jones himself (Bill Nighy, with a captivating squid puss), a seaport tavern brawl, the infamous East India Company (as the ultimate corporate villain), and a cannon-blasting sea battle. Plus Johnny Depp, pounding so hard on his Keith Richards imitation that it seemed inevitable Richards would be cast as his father in the next sequel. Best of the four, count ’em four movies based on a ride at Disney World.

Master and Commander: The Far Side of the World (2003)

Master and Commander: The Far Side of the World
Master and Commander: The Far Side of the World (Photo credit: Wikipedia)

Patrick O’Brian’s literate, seafaring Aubrey-and-Maturin novels finally hit the screen, by way of director Peter Weir. Napoleonic warfare, survival at sea, and meticulous period flavor are all subsumed, as they should be, by the two protagonists (played by Russell Crowe and Paul Bettany) and their ironclad, platonic bond to each other. Supposedly, 90 percent of the film was shot on the water.

The Imposters (1998)

After the 1930s, the luxury-ship-stowaway comedy fell, more or less, into remission until Stanley Tucci (who wrote, directed, and stars here) concocted this happy vaudeville about two lousy thespians (Tucci and Oliver Platt) who find themselves, quite by accident, on a cruise ship among European anarchists, spies, grieving ex-royalty, a pompous theater star (Alfred Molina), a suicidal nightclub singer named Happy Franks (Steve Buscemi), and sundry other broadly played types (including a Nazi-esque ship officer, triumphantly personified by Campbell Scott). It’s so unpretentious and dizzy, the entire cast conga-lines right off the set at the end, to boppin’ tango music.

The Lady Eve (1941)

The Lady Eve
The Lady Eve (Photo credit: Wikipedia)

Even if you’re the type who gets seasick in a wading pool, there’s something undeniably alluring about a 1940s cruise-ship liaison, and you’re not going to find a cuter and funnier dynamic than Barbara Stanwyck in a midriff-baring dress purring “Why, Hopsy!” at befuddled millionaire Henry Fonda. She’s part of a cardsharp trio out to fleece rich suckers, and he’s the chump. Preston Sturges wrote the devil out of this fluff in his customary fashion, and it might feature the hugest studio-built luxury boat ever dreamed up, with mansion-like ballrooms, sumptuous banquets, and endless moonlit decks.

China Seas (1935)

English: Publicity still
English: Publicity still (Photo credit: Wikipedia)

A voyage to Singapore during a typhoon might not usually sound appealing, but if Clark Gable is the ship’s captain, women will be stampeding the gangplank. He’s already spoken for by Jean Harlow, as a loosey goosey with a cast-iron mouth and a marshmallow heart. Her brash talk soon has the typhoon brewing on board as well, and he gives her the deep freeze and betroths himself to a British aristocrat. Shipboard shenanigans include an attack by Malay pirates, redeeming heroics, boozy sing-alongs with the officers, and a drinking game called Admiral Puff Puff Puff, which is probably fun even if you’re not playing with Jean Harlow in a clingy dress. The high China seas, by way of the MGM studio water tanks, knock the ship about and put the tough-talking fun in a pressure cooker.

Monkey Business (1931)

The four Marx Brothers stowing away on an ocea...
The four Marx Brothers stowing away on an ocean vessel by hiding in barrels in this promotional still for Monkey Business. Left to right: Harpo, Zeppo, Chico, Groucho. (Photo credit: Wikipedia)

The first and greatest comedy feature about stowaways on a cruise ship, this Marx Brothers farce is unbridled, high-octane silliness, but everyone is dressed to the Gatsby nines (except the gangsters, a newly popular archetype in 1931), and the childlike experience of simply running amok amid luxury-consuming adults is infectious. You might have fun on your own voyage, but not this much.

Eternal Sunshine of the Spotless Mind (2004)

This Chinese-box mystery is actually a romantic comedy—albeit one that’s been Rubik’s Cubed and set adrift in an unmoored consciousness by Charlie Kaufman’s beautiful screenplay. Jim Carrey stars as a shy nebbish in love with Kate Winslet’s bipolar tramp; once dumped, he seeks out a small firm that will literally wipe his memories of her right out of his brain. Of course, it’s not that easy, and neither is the film, since much of it takes place in a beleaguered subconscious that’s being technologically erased as we watch. In the end, though, the lovelorn mood trumps the gimmickry.

The End of the Affair (1999)

The End of the Affair (1999 film)
The End of the Affair (1999 film) (Photo credit: Wikipedia)

Adapted from the Graham Greene novel and filmed by Neil Jordan with all the intelligence that work requires, this is all about wartime love (between married woman Julianne Moore and family friend Ralph Fiennes) as a defiance of—and, finally, a bloody deal made with—a hard-bargaining God. One of the best British films of the 1990s, and predictably underappreciated.

Chungking Express (1994)

Wong Kar-Wai is world famous for his fractured, lovelorn fairy tales, which buzz around Hong Kong and trail after young, lonely obsessives who are strung out on unsuccessful coping strategies and searching for love in every wrong corner. This popular mini-masterpiece is actually divided into two equally significant stories, in which two city cops struggle with heartbreak and magical thinking. Similar, and also recommended, are Wong’s Fallen Angels (1995), a more complex interwoven narrative, also full of post-noir fatalism and urban melancholy, and Happy Together (1997), a doomed gay romance playing itself out in the hothouse of a Buenos Aires flop-joint. Subtitled.

Brief Encounter (1945)

Cover of "Essential Art House: Brief Enco...
Cover of Essential Art House: Brief Encounter

Scored to Rachmaninoff, this world-famous Noël Coward–David Lean tragedy-in-a-teapot recounts, simply, the doomed romance between a conventional British housewife (Celia Johnson) and a conventional British doctor (Trevor Howard), each of whom is married to someone else. Nothing dramatic happens between them, and that’s the picture’s deliberate strategy—it summons the pathos of what doesn’t occur, as opposed to what disastrously might’ve been.

How Green Was My Valley (1941)

The well-read Richard Llewellyn novel by way of director John Ford, this portrait of Welsh coal-mining country gets you right here. Packed with Ford’s Celtic stock company of actors, including Maureen O’Hara, plus Walter Pidgeon as a schoolteacher, Oscar winner Donald Crisp as Dad, and Roddy McDowall as the family’s youngest son.

Fever Pitch (2005)

Fever Pitch (2005 film)
Fever Pitch (2005 film) (Photo credit: Wikipedia)

Perhaps date movies shouldn’t be about people who are dating at all, since films that focus on relationship strife provoke questions of rights and wrongs, guilt and innocence that viewers on a date might not want to get into. At least Fever Pitch (which is based on a much more cynical Nick Hornby novel that revolves around English football, not baseball) is relatively innocuous in this regard, if only because the main characters are both so adorable: Late Night TV favorite Jimmy Fallon is Ben, a humble schoolteacher who loves his job and the Boston Red Sox; Drew Barrymore is Lindsey, a high-powered business genius who’s looking for something better than the shallow corporate climbers she usually dates. Trouble occurs when she starts realizing that Ben just might not consider her as important as a bunch of overpaid jocks. (Note to male viewers: the correct response to this realization is not, “Yeah, so?”) The movie includes cameos by some of the 2004 Sox—who beat the odds and earned Boston a World Series victory for the first time in eighty-six years. (The last scenes of the film were rewritten and shot during the series to capitalize on this amazing turn of events—who coulda thunk it?).

Out of Sight (1998)

This might well be the best date movie ever made. You could watch this Elmore Leonard adaptation, in which George Clooney and Jennifer Lopez flirt like they’re in heaven together, again and again; it’s a perennial, and it’s inexhaustibly brimming with character bits, witty dialogue, and narrative invention. Crooks, cops, heists, and so on abound—but this movie is less about the plot than it is about the people—and that’s what dating’s about, really, isn’t it?

Jerry Maguire (1996)

Jerry Maguire
Jerry Maguire (Photo credit: Wikipedia)

A romantic comedy about a sports agent is, in concept, kind of like a musical about an arms dealer, but Cameron Crowe’s hit remains refreshingly witty, sharp, affecting, and—glory of glories—slick without being trite. A pleasurably humane and light-footed stroll through familiar territory, the movie at times smacks of a Ron Shelton or Paddy Chayefsky satire on the agenting industry, but in the end it’s too starry-eyed by half for that. Let’s face it: Tom Cruise is usually too good-looking and supercilious to be convincing as a normal, modest human being, but here, as a go-getter agent whose bread and butter are his empty smile and his spiel, he’s superb—suddenly, all of that self-love and amoral charm makes perfect sense. The dramatic crux is the hero’s midcareer crisis of integrity—a fit of self-loathing impels Maguire to write a “more heart, less profit” memo and distribute it around his bustling agency’s office. Of course, he’s summarily fired, but he manages to convince single-mom accountant Dorothy (Renee Zellweger) to come with him to help start up his own business. All of his clients drop him; all but one, that is—showboat Rod Tidwell (Cuba Gooding Jr., who won an Oscar for it), a wide receiver with more attitude than talent. Jerry Maguire may be the most femme-friendly sports movie ever made, and it manages that feat without resorting to bathos.

Before Sunrise (1995)

Jesse and Celine (Ethan Hawke and Julie Delpy), each alone and separately heartsick, meet on an aimless train ride through Austria, and decide to disembark and spend a day talking. That’s all there is to it—or, almost all—and yet this impossibly brilliant, moving film is a perfect date movie. Actually, it might be too perfect—does it raise expectations too high regarding just-met sparkling conversation, witty sex appeal, and intelligent soul sharing? Jesse and Celine seem preposterously and blissfully well suited for each other, no matter how messily realistic Richard Linklater’s screenplay is about emotional exchange—could their ease and confidence intimidate the naturally nervous dater? Perhaps—or maybe it’d help boil the water and get the gears greased. The socially handicapped might consider it a form of basic training to view this movie on (or even before) a date. Pay attention, pilgrims: this is how it is done. Better than its sequel, Before Sunset, and far, far better than the third time at bat with these characters, Before Midnight.

Defending Your Life (1991)

Cover of "Defending Your Life"
Cover of Defending Your Life

Once, Albert Brooks was the ultimate everyman schlemiel; here that schlemiel dies, and he’s uncomfortable even in the afterlife. This is a date movie? Well, he meets Meryl Streep, the only other recently deceased person under seventy, and as they each attend hearings before a purgatorial tribunal to examine their lives and determine if they have exhibited enough courage to “move forward” (think of it as Beverly Hills Buddhism), they fall in love, even though there’s no hope that they can ever be together. This is an especially appropriate film for nascent relationships—it’s funny but not raunchy, cute but not sticky. It’s probably best to plan for a dinner afterward; one of the clear benefits of spending time in Judgment City (which looks remarkably like Southern California) is that you can eat as much as you want and never gain weight, so there’s plenty of moaning over mounds of shrimp and piles of pasta.