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There’s nothing like an anniversary — especially a milestone like 50 years. And as we head into 2019, we’ve decided to take a look back at some of the biggest films that will be celebrating their half-century mark this coming year, including movies from stars like Paul Newman and Robert Redford (Butch Cassidy and the Sundance Kid), Clint Eastwood (Paint Your Wagon), Jon Voight (Midnight Cowboy), Barbra Streisand (Hello Dolly!), John Wayne (True Grit), and Dean Martin (The Wrecking Crew).
The truth is, in many ways 1969 was a turning point for Hollywood, with filmmakers pushing the creative envelope in terms of content (the spouse-swapping Bob & Carol & Ted & Alice), the way movies were made (Easy Rider, shot on a shoestring budget with little in the way of a script, but turning into a giant box office hit), the exploration of violence (The Wild Bunch), and shaking up the tried-and-true (George Lazenby replacing Sean Connery as James Bond in On Her Majesty’s Secret Service).
To join us on this trip to the past and to check out all of these and more, just scroll down below.
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National General Pictures
‘A Boy Named Charlie Brown’
The first movie based on Charles M. Schulz’ beloved characters sees a rare win for old blockhead when he is the champion of the school spelling bee. This leads him to the National Spelling Bee in NYC. Can his luck hold up? C’mon, this is Charlie Brown we’re talking about. Argh!!
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GAB Archive/Redferns
‘Bob & Carol & Ted & Alice’
Nineteen-sixty-nine was a time when movies really began pushing the envelope, and this film was an early indication of it. Robert Culp and Natalie Wood are Bob and Carol Sanders, who, following a weekend of emotional honesty at a unique retreat, end up having affairs with other people that are purely physical, and not emotional. And they’re okay with this, to the point where their best friends, Ted and Alice Henderson (Elliott Gould and Dyan Cannon), get caught up in the whole idea of partner-swapping. But is it everything the foursome think it will be?
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Movie Poster Image Art/Getty Images
‘Butch Cassidy and the Sundance Kid’
One of the great team-ups in Hollywood history, with Paul Newman and Robert Redford as the Wild West outlaws of the title. There’s train and bank robberies aplenty, gun battles, and so much more, but the real magic is watching Newman and Redford play off each other (as they would again several years later in The Sting).
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Walt Disney
‘The Computer Wore Tennis Shoes’
Kurt Russell is student Dexter Reilly who is working on repairing a computer during an electrical storm, when he finds his brain fused with the machine’s following a massive shock. Suddenly he’s a genius with all the knowledge that was within the computer, including the fact that the businessman who donated it (Cesar Romero’s A.J. Arno) is a crook, which puts his life in (old-style Disney) danger.
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Silver Screen Collection/Hulton Archive/Getty Images
‘Easy Rider’
Google describes this one as follows: “Wyatt (Peter Fonda) and Billy (Dennis Hopper), two Harley-riding hippies, complete a drug deal in Southern California and decide to travel cross-country in search of spiritual truth. On their journey, they experience bigotry and hatred from the inhabitants of small-town America and also meet with other travelers seeking alternative lifestyles. After a terrifying drug experience in New Orleans, the two travelers wonder if they will ever find a way to live peacefully in America.” Many people asked the same thing about Hollywood in the aftermath of this film, which was made for $400,000, grossed $60 million and was made with a naturalness and spontaneity that the “system” had no idea how to respond to. Co-writer and star Peter Fonda viewed this as a modern-day Western that embraced the counter-culture movement of the time.
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Ernst Haas/Ernst Haas/Getty Images
‘Hello Dolly!’
Based on the Broadway musical of the same name, Barbra Streisand is Dolly Levi, an 1890’s matchmaker who travels to Yonkers, New York, to find a romantic partner for Horace Vandergelder (Walter Matthau), described as “half-a-millionaire.” The film won three Oscars for Best Art Direction, Best Score of a Musical Picture, and Best Sound.
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Columbia/Getty Images
‘Marooned’
Released only five months before the near-disastrous Apollo 13 mission, this film postulated a mechanical malfunction that strands three astronauts (played by Richard Crenna, Gene Hackman, and James Franciscus) in Earth orbit aboard their spacecraft, as NASA tries to engineer a rescue mission before they run out of oxygen. Genuine tension is created by director John Sturges.
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Liaison Dist./Liaison
‘Midnight Cowboy’
The first “X”-rated film released by a mainstream studio (more because of subject matter and profanity rather than anything you’d normally slap an “X” rating on). A disturbing character study, it sees Jon Voight as Joe Buck, a naive hustler who travels from Texas to New York dreaming of using his charm and looks to score from a rich widow, but finds himself going down a dark path, including male prostitution. He does bond with another conman, “Ratso” Rizzo (Dustin Hoffman), the two of them forming an unlikely alliance and then friendship. The film took home a trio of Academy Awards in the categories of Best Picture, Best Director (John Schlesinger), and Best Adapted Screenplay.
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MGM
‘On Her Majesty’s Secret Service’
After filming five James Bond adventures, Sean Connery had had enough and dropped out of the film series. In his place came Australian model George Lazenby, who handles himself far better than anyone could have expected him to. While far from embraced when it was originally released 50 years ago, OHMSS (as it’s more popularly known) is regarded as one of the best Bond films ever. It also stars Diana Rigg as the only woman that 007 ever married. A combination of great action, story, and an actual character arc(!).
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Paramount Pictures
‘Paint Your Wagon’
Proof positive that not every Broadway musical needs to be adapted into a movie. Set during the Gold Rush in California, Clint Eastwood and Lee Marvin are prospectors who look to get rich. You ain’t lived none ’til you dun heard Eastwood and Marvin sing. Somehow it didn’t connect with the audience. Hmm.
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Sunset Boulevard/Corbis via Getty Images
‘Take the Money and Run’
After writing, dubbing, and editing a Japanese film in the form of What’s Up, Tiger Lily?, Woody Allen makes his full-fledged debut as performer and writer/director on this film. In it, he launches his nebbish portrayals as Virgil Starkwell, whose dream is to become a notorious bank robber, which he is miserable at. Great early comic fun from Woody!
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Sunset Boulevard/Corbis via Getty Images
‘True Grit’
Kim Darby is 14-year-old Mattie Ross, who, in the aftermath of her father’s murder, hires U.S. Marshall “Rooster” Cogburn (played by the legendary John Wayne) to track down his killer through Indian territory and bring him to justice. John Wayne took home Best Actor honors from the Golden Globe and Academy Awards. There was a 1975 sequel, Rooster Cogburn, with Wayne reprising his role; and a 2010 remake starring Jeff Bridges.
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Cinerama Releasing Corporation
‘Whatever Happened to Aunt Alice?’
This is a complete guilty pleasure that few people probably remember. Ruth Gordon is Alice Dimmock, the employer of a housemaid to Claire Marrable (Geraldine Page), who has gone missing (as have many of the woman’s other housekeepers). Alice goes undercover as a maid herself trying to discover the truth, not realizing she’s putting herself in deadly danger.
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Silver Screen Collection/Getty Images
‘The Wild Bunch’
Sam Peckinpah’s classic Western about aging outlaw Pike Bishop (William Holden), who is preparing to retire after one final robbery. Joined by his gang (played by Ernest Borgnine, Warren Oates, and Ben Johnson), he discovers that the heist has been undermined by former partner Deke Thornton (Robert Ryan). The resulting shoot-out turns violence into an art form.
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Columbia Pictures
‘The Wrecking Crew’
We have to admit, the inclusion of this one’s a bit of a cheat, because it was released on Dec. 30, 1968, but any excuse to include the King of Cool (even if it’s in this film)! With the success of the James Bond films impacting the ’60s, the decision was made to take Donald Hamilton’s gritty character of Matt Helm and turn him into a swinger in the form of Dean Martin. This was the fourth in the series and it’s pretty awful, but the truth is: they don’t make ’em like this anymore and there is some nostalgic fun to be had here. Some.

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