‘Mad Men’ Multiplex: Which 1969 Movies Will Turn Up This Season?

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From the third-season cola campaign aping Bye Bye Birdie to last year’s multiple screenings of Planet of the Apes, Mad Men has always dipped generously into the pool of period cinema to help set its scene, while simultaneously drawing inspiration from films of the era (The Apartment, BUtterfield 8, Will Success Spoil Rock Hunter, and How to Succeed in Business Without Really Trying — starring Bert Cooper himself, Robert Morse — leap to mind). We’ve taken some guesses at the books this season’s 1969 timeframe might introduce; here are a few of the most popular movies of that year, and how they might work their way into Don Draper’s world.

Midnight Cowboy

The second-highest-grossing movie of the year, and the Academy Award winner for Best Picture (the only X-rated movie to ever achieve that honor), John Schlesinger’s adaptation of James Leo Herlihy’s novel took full advantage of the newfound freedom of the New Hollywood movement, presenting a story of sexual ambiguity and narrative maturity — exactly the kind of storytelling that Mad Men’s team values so highly. It also gave moviegoers a look at exactly how seedy New York City had become; we expect to see that gritty visual aesthetic replicated this season, and the chances of hearing the movie’s ubiquitous theme song, “Everybody’s Talkin’,” are very high indeed.

Bob & Carol & Ted & Alice

Your film editor’s favorite movie of 1969 is Paul Mazursky’s delicate, penetrating, and uproarious comedy of manners, in which two couples (played to perfection by Natalie Wood, Robert Culp, Elliot Gould, and Dyan Cannon) leap headfirst into the sexual revolution, only to discover they’re maybe not as hip as they thought. Could Don decide to make his philandering legit by doing a bit of swinging with Megan? (Last season’s encounter with the swinging producer and co-star of her soap doesn’t indicate much openness, but hey, the times are changing, and people do too.)

Easy Rider

But the pop-culture sensation of 1969, cinematically speaking, was Dennis Hopper’s rock ‘n’ roll biker pic, made on a tight $360,000 budget, which spun into a $41 million gross. I could see the movie showing up as either a) a Bye Bye Birdie-ish rip-off campaign, swiping the movie’s iconography and style, or b) a return appearance by Paul Kinsey, bearded and leather-clad, atop a California-style chopper.

True Grit

It seems pretty safe to bet that Don won’t turn out to be an Easy Rider fan; if we learned anything from his encounter with the Beatles’ “Tomorrow Never Knows,” it’s that the man is a bit of a conservative, culturally speaking. The year’s seventh-biggest-grossing movie, True Grit, seems more like his speed — a classic Western starring John Wayne, whose iconic turn as Marshall “Rooster” Cogburn finally nabbed him an Oscar for Best Actor.

Butch Cassidy and the Sundance Kid

1969’s biggest movie at the box office — by a long shot, taking in more that double the gross of #2 Midnight Cowboy — was George Roy Hill’s buddy Western comedy, which gave Paul Newman yet another giant hit, while successfully pairing him with an up-and-comer named Robert Redford. (Fun fact: Sam Elliot made his film debut here, as “Card Player No. 2.”) But even this period comedy wasn’t immune from what Roger Ebert dubbed the “Semi-Obligatory Lyrical Interlude,” and defined as a scene “in which soft focus and slow motion are used while a would-be hit song is performed on the soundtrack and the lovers run through a pastoral setting.” In Butch Cassidy, it was the “Raindrops Keep Fallin’ on My Head” sequence; it wouldn’t be surprising to see a similar style start showing up in Sterling Cooper & Partners’ ads this season.

The Wild Bunch

It was a big year for Westerns, and Sam Peckinpah’s subversive, ultra-violent oater was highly controversial when it was released in the summer of ’69. But it wasn’t just the bloodshed that got people’s attention; it was the director’s use of quick cuts, multiple angles of action, and juxtaposition of normal and slow motion, a style that would influence not just cinema, but advertising forevermore.

Take the Money and Run

In August of 1969, Cinerama released this crime comedy, the feature directorial debut (aside from the repurposed lark What’s Up Tiger Lily ) of nightclub comic-turned-screenwriter Woody Allen. It’s an amusing picture that did decent box office — but more importantly, it was one of the first feature comedies to adopt the “mockumentary” style, employing the documentary tropes of talking-head interviews, handheld camerawork, and hardboiled narration for comic effect. Such tricks would turn up frequently in films and ads in the years to come.

The Stewardesses

There’s a fascinating story behind this long-forgotten title, which came in at #14 in the year-end box office tally — ahead of such classics as Once Upon a Time in the West, The Wild Bunch, Topaz, and They Shoot Horses, Don’t They? Writer/director/co-producer Allan Silliphant (brother of In the Heat of the Night writer Sterling) originally released this $100,00 3D skin flick with a self-applied X rating. But as it became an adult hit, he and his team set about shooting new scenes, adding production value, and softening the sex, remaking the film — while it was in release, mind you — as a hard-R movie for general consumption. Over the course of its three-year release, it went through four different variations, playing respectable theaters and grossing a total of $25 million. In other words, it was the dirty-movie sensation of the pre-Deep Throat era, and the kind of flick Roger Sterling might slip out of the office one afternoon to catch at a matinee.