Billy Wilder is the greatest screenwriter in film history. No need for a qualifier like ‘one of.’ His movies range from gritty film-noir to screwball comedy, with stops in all manner of genres in between. He worked with several writing partners, but no matter the subject or the collaborator, his screenplays are always good and often extraordinary. Wilder’s directing style reflects his writing, emphasizing story over style, something many of today’s filmmakers could learn from. If you have not had the pleasure of diving into his catalog, I envy you the chance to embark on a once in a lifetime filmgoing journey. Here are the top ten Billy Wilder movies I think you should start with and a suggested order to watch them.
Three Films to Get Started
Some Like It Hot
Billy Wilder liked to push the envelope of what a film could get away with. In 1959, a comedy about two male musicians on the run from the mob posing as members of an all-female band was scandalous. Tony Curtis and Jack Lemmon cross-dressing hinted at homosexuality. The raw sexual presence of Marylyn Monroe was too risqué. The keepers of the Production Code (a precursor to the rating system) decided not to grant a Certificate of Approval. By the late 50s, many theaters didn’t care and still screened the movie, though it was banned in one state for being “too disturbing for Kansans.” While tame by today’s standards, the film is still hilarious. It’s number one on the American Film Institute’s top 100 funniest movies list. It also features the best last line in film history. Do yourself a favor and don’t spoil it before you see it.
The Apartment
Like Some Like It Hot, Wilder co-wrote The Apartment with I.A.L. Diamond, the only writing partner he had during the last third of his career. The two of them were remarkably skilled at combining comedy and drama. This film is the best example of their magic. Jack Lemmon plays a corporate schlub who lets superiors use his apartment for illicit trysts with their mistresses. Shirley MacLaine is the elevator girl he’s secretly in love with. Wilder often tried to cast actors against type and called on clean-cut Fred MacMurray, whose last major movie had been Disney’s The Shaggy Dog, to play the office bigwig who complicates matters. Both a satire of corporate politics and an incisive look at love and loneliness, The Apartment propelled Wilder to Oscar wins for producing, writing and directing.
Sunset Boulevard
This story of a forgotten silent movie star who makes a struggling screenwriter into her kept man is Wilder at his most darkly comic. Gloria Swanson was a fading star of the silent era given the role of a lifetime. When she exclaims, “I am big, it’s the pictures that got small!”, Swanson could just as easily have been talking about herself. William Holden jumped at the chance to star as the screenwriter in the first of several films he made with Wilder. The movie itself feels far ahead of its time, taking on with a vengeance how easily Hollywood throws away its past. Even though many in Tinsel Town were not amused, the film still won an Oscar for its screenplay. Some enterprising studio could take a former big name like Faye Dunaway and cook-up a modern-day remake without too many changes. Don’t tell them though. Odds are they would.
Four Films to Keep Going
Sabrina
Billy Wilder’s most romantic film features an unlikely love triangle of Audrey Hepburn, William Holden, and Humphrey Bogart. In another of his cast against type strokes of brilliance, Wilder convinced Bogart to play a stuffy businessman. Bogie was not comfortable in the role, but that likely helped his performance as the uptight older brother to Holden. When the younger brother thinks of leaving his fiancé for Hepburn’s inviting title character, a profitable business opportunity is put at risk. Bogart has to steer them apart and turns his attention to Sabrina. Of course, he falls for her. A confection of style and romance bakes together to make the movie irresistible.
Sabrina was co-written by Ernest Lehman, who also features in my top ten movies of Alfred Hitchcock list for a very different kind of film.
Stalag 17
Holden won an Academy Award for his third collaboration with Wilder on my list. This World War II picture combines comedy, drama, and mystery in a taut tale about finding a traitor among American soldiers in a prisoner of war camp. Holden’s character is the most cynical and independent of the group, so naturally, suspicion falls squarely on him. In an unusual move, Wilder shot the film in chronological order, keeping the identity of the mole secret to most of the cast right up until the end. Wilder was adept at both original and adapted scripts. Stalag 17, which he co-wrote with Edwin Blum, was based on a long-running Broadway show. Both the Steve McQueen classic film The Great Escape and the 1960s sitcom Hogan’s Heroes took quite a bit of inspiration from this one.
Double Indemnity
Co-written with Raymond Chandler and based on a book by hardboiled writer James M. Cain, this quintessential film noir is about an insurance salesman who cooks up a scheme with his mistress to kill her husband. The upstanding citizens at the Production Code had numerous problems with the plot and required considerable re-writing. Many actors refused to be associated with the film. Like later with The Apartment, Wilder convinced nice guy Fred MacMurray to play a shady character. Barbara Stanwyck, Hollywood’s highest paid actress at the time, overcame her reservations to co-star. Edward G. Robinson is also in top form as an insurance claims investigator unraveling their scheme. The film’s dialogue crackles unlike almost anything else from the era. The “venetian blind” lighting became a staple of the genre. Double Indemnity leaves a gritty taste in your mouth that lingers.
The Fortune Cookie
Before The Odd Couple, Jack Lemmon and Walter Matthau teamed up in this black comedy. Wilder loved football, and it shows in the film. Lemmon is a cameraman who is injured on the sidelines by Luther “Boom Boom” Jackson, star running back for the Cleveland Browns. His injuries are minor, but Matthau as his brother-in-law, a lawyer nicknamed Whiplash Willie, convinces him to play things up and milk the situation for all it’s worth. Lemmon’s character and “Boom Boom,” nicely played by an actor named Ron Rich, develop a friendship. Complications ensue when guilt starts to impact the running back both on and off the field. Matthau suffered a heart attack during filming but recovered to complete the shoot and win an Oscar for Best Supporting Actor.
Three Films to Dig Deeper
One, Two, Three
Early in his Hollywood career, Wilder co-wrote the script to Ninotchka, a comedy starring Greta Garbo about a communist apparatchik corrupted by the west in Paris. One, Two, Three has echoes of that film’s cold war themes and temperament. James Cagney of all people plays a Coca-Cola executive in Berlin trying to expand operations into the Soviet Union. When his boss’ daughter shows up and gets engaged to a communist officer, hilarity ensues. Wilder wanted to make “the fastest picture in the world,” and the movie operates at the frantic pace of the best screwball comedies. Cagney is a marvel of energy and was so burned out after the shoot, he quit acting for twenty years. Wilder and crew were filming in the city the morning the Berlin wall went up. Production moved to Munich for completion.
The Lost Weekend
Billy Wilder’s other Best Picture winner is this story of a struggling writer’s battle with alcohol over a long weekend. Wilder co-wrote this with Charles Brackett, the primary writing partner in the early part of his early career. They won an Oscar for the film’s script. The movie also took home Oscars for direction and for leading actor Ray Milland. While somewhat dated, it’s still a brutal look at alcoholism. The liquor industry tried to undermine the movie before its release. Rumor is that a mob boss approached Paramount Pictures offering $5 million for the film’s negative so he could burn it. Wilder would later quip that if they offered him the money, he would have burned it himself.
Ace in the Hole
This picture was Wilder’s first major commercial failure. Kirk Douglas plays a reporter whose fading big city prospects force him to a newspaper in Albuquerque. He eagerly looks for a big story that will catapult him back to prominence. It falls in his lap when a man becomes trapped in a cave while prospecting for relics. Douglas’ character manipulates the man’s wife and a local sheriff, conspiring to keep the man trapped long enough for the story to earn him a ticket back to New York. The film’s cynical eye, aimed squarely at the power of the press to manipulate a gullible public, was decades ahead of its time. Critical reaction upon released scoffed at how it tore down the trustworthy media. Later critics have rightly noted how topical the story seems today. Sensing box-office trouble, Paramount changed the name of the film to The Big Carnival. More recent video releases have reverted back to the much better original title.
Final Thoughts on Billy Wilder and My Top Ten List
The most iconic shot in Billy Wilder’s filmography is of Marilyn Monroe standing on a subway grate with her white dress billowing up. I love the above picture of Wilder directing that scene. This amazing piece of cinema history is from The Seven Year Itch, which would have made my list if I included a dozen movies. Almost all of Wilder’s films are worth a watch. Witness for the Prosecution, The Private Life of Sherlock Holmes, The Spirit of St. Louis, and Five Graves to Cairo would round out my top fifteen.
Most of the films in my top ten are available for streaming on one platform or another for a small fee. I could only find The Fortune Cookie for free on Amazon Prime. One, Two, Three was the only film I couldn’t find on any platform, though it shows on TCM from time to time and you can get it on disc.
The great people at the Criterion Collection have put out blu-rays of both Some Like It Hot and Ace in the Hole. As with any Criterion release, they are well worth it. Another excellent DVD company is Arrow Video. Their blu-ray release of The Apartment is one of the most beautiful black and white transfers I have ever seen, though be prepared to pay through the nose!
Late in his life, Wilder sat down for a series of interviews with filmmaker Cameron Crowe, the writer and director of Jerry Maguire and Almost Famous. Crowe unsuccessfully tried to get Wilder to play a small part in Jerry Maguire. His book Conversations with Wilder was very helpful to the making of this list and is a great read for anyone interested in Billy Wilder or classic Hollywood.
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