‘Sunset Boulevard’ Director Billy Wilder’s Iconic Films Define Hollywood’s Golden Age
In the hall of great filmmakers, Billy Wilder stands as one of the most influential directors in Hollywood history. When the restrictive censorship codes forced films to embrace simplistic plotting with a black-and-white morality, Wilder crafted provocative tales filled with shades of grey. A Wilder production often featured protagonists who were flawed, complex, and remarkably human among a sea of matinee heroes and mustache-twirling villains that populated the classic era.
Wilder started as a screenwriter and became one of the few directors to write his movies, forbidding actors to change a syllable of his expertly crafted texts. Wilder had an ear for bold, incisive dialogue, giving his many classics a modern tone.
Looking at the movies below, this director worked in nearly every genre, easily moving between drama, romance, screwball comedy, film noir, and sharp satire.
Ninotchka (1939)
Wilder found early success by co-writing (with Charles Brackett and Walter Reisch) the classic Greta Garbo comedy. Directing duties fell to iconic rom-com director Ernst Lubitsch, and he fills Ninotchka with his clever, whimsical flourishes. In one of her final screen appearances, Garbo plays a stern Soviet fixer sent to Paris to supervise the sales of jewels seized from Russian nobles but falls for Count Leon, a man who represents the ills of capitalism.
Lubitsch’s fingerprints are all over Ninotchka, but Wilder’s sharp script bubbles through the romance, particularly in Garbo’s deadpan replies to the smitten Leon. Garbo rarely strayed from her grand melodramatic roles, but her pairing with Wilder’s script showed she had strong comedic chops. Wilder also managed to mix in a political skewering of the Soviet Union’s communist leanings, a prelude to the Cold War that would start in the next decade.
Double Indemnity (1944)
Wilder crafted what is now considered one of the great film noirs of all time with Double Indemnity. The director co-wrote the script with legendary writers Raymond Chandler and James M. Cain. that chronicles an L.A.-based insurance rep who’s seduced by an alluring housewife into killing her husband so they can collect his life policy money. The brilliant screenplay crackles with noir-laced dialogue, including the much-imitated “there’s a speed limit in this state” exchange.
Barbara Stanwyck and Fred MacMurray's performances enhance the film’s lurid subject matter by highlighting their characters' loathsome traits. Stanwyck, in particular, gives one of the great femme fatale moments with her cold stare as she hears her husband being murdered behind her. Wilder frames the proceedings with stark black-and-white angles and shadows that would become standards of the film noir.
The Lost Weekend (1945)
Wilder won his first Best Directing Oscar (along with Best Picture) for this bleak exploration of alcoholism. The Lost Weekend follows a failed writer whose life spirals out of control when he goes on a four-day bender. This was a dark subject matter to tackle due to the surge of alcoholism in post-War World II America. Many soldiers began suffering the effects of PTSD. In fact, the executives at Paramount Pictures feared they had a massive flop on their hands, only to be pleasantly surprised that The Lost Weekend became the rare critical and commercial smash.
British actor Ray Milland gives a powerful (and Oscar-winning) performance that makes The Lost Weekend an engaging watch. Wilder frames the picture as a thriller, wondering what obstacles will sink Milland further into his alcohol-fueled stupor. Sadly, Wilder had to stamp the film with a patented happy ending, but The Lost Weekend remains a snapshot of how America viewed the ravages of alcoholism in the 1940s.
Sunset Boulevard (1950)
Wilder started his most successful decade as a filmmaker by releasing the film that would epitomize his career: Sunset Boulevard. This cynical antidote to the technicolor “happy ending” fantasy deconstructs Hollywood by focusing on the silent majority who never attain their Tinseltown dreams. Sunset Boulevard explores two eras of Hollywood colliding when failed B-Movie writer Joe Gillis becomes ensnared by the crazed Norma Desmond, a forgotten starlet from the silent era still clinging to a career that has passed her by.
Sunset Boulevard features one of the great stunt castings of all time. Wilder coaxed silent film legend Gloria Swanson out of retirement to play the tragic, almost caricature-like Norma, whose Hollywood dreams shattered with the onset of the talkies. Her spellbinding meta performance, full of wild eye and hand movements, gives the film noir a gothic, operatic tone. It’s no surprise that populist composer Andrew Lloyd Webber adapted the movie into a successful Broadway musical starring Glenn Close.
Sunset Boulevard also explores the lifestyle of the working screenwriter, an invisible and underappreciated ingredient of the filmmaking process. William Holden’s performance as Joe Gillis, who matches Swanson beat for beat, perfectly displays the world-weariness of a writer hustling for his next gig. One can sense that Gillis stands-in for Wilder himself, highlighting the highs and lows of writing dialogue that turns actors into stars.
Ace in the Hole (1951)
Wilder amplified the cynicism for his follow-up feature to his great classic, Ace in the Hole. Kirk Douglas plays Chuck Tatum, a washed-up big-city journalist working at a tiny Albuquerque newspaper. But when a man becomes trapped in an abandoned Indian dwelling cave, Tatum exploits the tragedy by leading the rescue effort and feeding sensational stories to the media. Soon, the story turns into a media circus that Tatum intends to milk for all its worth.
Ace in the Hole is arguably Wilder’s most stark film, filled with characters eager to set aside their morality to make a quick buck. Douglas plays Tatum with an unsympathetic sneer fueled by his desire to regain his once lofty perch as an A-list reporter. The film’s storyline remains relevant today in this media landscape dominated by “breaking news” headlines and social media influencers becoming stars by hawking merchandise online.
Stalag 17 (1953)
Wilder reteamed with his Sunset Boulevard star William Holden in this comedic thriller set inside a German POW camp during the final days of World War II. In his Oscar-winning performance, Holden plays JJ Sefton, a black marketeer for the barracks who enjoys his goods and privileges. When two Americans are killed during an attempted escape, all signs point to an informer tipping off the guards. Soon, a mob mentality takes over the barracks, where they decide that Sefton is the traitor, forcing Sefton to clear his name by finding the actual perpetrator.
Wilder performs quite the juggling act of melding the classic murder mystery with comedic overtones set inside a prison camp during World War II. The director heavily reworked the famous stage play the film was based on with co-writer Edwin Blum, lacing the darker moments with black comedy. While watching Stalag 17, one might recall the classic sitcoms Hogan’s Heroes and MASH, both of which liberally borrowed from the tone set by Wilder’s smart adaption.
Sabrina (1954)
The director returned to the romantic comedy with Sabrina, a modern fairytale starring Audrey Hepburn, Humphrey Bogart, and (once again) William Holden. Hepburn plays the title character, the charming daughter of the chauffeur for the wealthy Larrabee family, who catches the eye of the family’s aristocratic charmer, David Larrabee. When this pairing could derail a profitable corporate merger, the older brother Linus steps in to woo Sabrina himself, falling in love with her in the process.
One senses that Wilder crafted this champagne-like confection to take a break from his previous films' bleak, cynical tone. While the film mainly works due to Hepburn’s romantic charisma, the age disparity (30 years!) between her and Bogart will be hard for modern audiences to accept. Also problematic is that Hepburn shares fantastic chemistry with her other co-star, Holden, warping the romantic triangle. In fact, Holden seems to be having the time of his life by playing the superficial aristocrat, which makes him a far more interesting character to watch.
In 1995 Sabrina received a well-regarded remake with Harrison Ford and Julia Ormond in the lead roles. This version does a better job of ironing out the relationship's May-December nature, featuring Ford in his handsome, comedic prime as the older brother Linus.
The Seven Year Itch (1955)
Wilder directed one of Marilyn Monroe’s most iconic moments in his adaptation of George Axelrod’s stage comedy The Seven Year Itch. The story follows New Yorker Richard Sherman, who longs to return to his bachelor ways when his family leaves on their annual summer vacation. But soon, his ditzy, beautiful neighbor tempts his amorous and overactive imagination. Monroe’s famous moment comes midway through the movie when the cool air from a subway grate blows up her white skirt as Sherman delightedly watches.
The Seven Year Itch has not aged well since its 1955 release, but this remains one of Monroe’s best comedic roles. Despite her difficulties on set, Wilder was one of the few directors who could channel her singular persona to great effect. Character actor Tom Ewell deserves mention too, playing his daffy family man like a deer in the headlights when facing the stunning Monroe.
Witness for the Prosecution (1957)
Agatha Christie and Billy Wilder proved a potent combination when he helmed the film version of the play adapted from her short story “Traitor’s Hands.” Wilder assembled an impressive cast featuring Charles Laughton, Marlene Dietrich, and Tyrone Power in his last screen role before his tragic death in 1959.
Laughton plays ailing barrister Sir Wilfred Roberts, who’s lured back into the courtroom to defend Leonard Vole, a poor inventor charged with the murder of a wealthy older woman. The earnest and friendly Vole appears innocent, but questions arise when his cold-hearted wife agrees to appear in court against her husband.
Witness for the Prosecution features the expert plot mechanics of an Agatha Christie mystery, particularly around Vole’s innocence. Wilder and Dietrich make a great pair, and the German beauty with the ice-blue eyes plays the femme fatale like an ace wild card that keeps the twists and turns coming. The plot nearly collapses during the final ten minutes, where surprise twist after twist pushes the limits of believability. But Wilder’s skill behind the camera makes viewers buy into the illusion.
Some Like It Hot (1959)
Despite her challenging offscreen behavior, Wilder reteamed with Marilyn Monroe in Some Like It Hot, which would become her most famous film. The influential screwball comedy stars Jack Lemon and Tony Curtis as two hapless musicians who, after witnessing a mob hit, disguise themselves as women in a traveling all-girl band. But comedic hi-jinks ensue when they befriend the lustrous Sugar Cane, who sings and plays the ukulele for the band.
When Some Like It Hot opened in 1959, it became a commercial and critical smash that earned six Oscar nominations. The film has since earned with acclaim as one of the greatest screen comedies of all time, launching a subgenre of gender-bending movies that continues today. The movie works mainly due to the strength of its three lead actors, who are in top comedic form. Monroe never looked more alluring on screen, especially when wearing the famous silk dress, which doesn’t leave much to the audience's imagination.
The Apartment (1960)
Wilder closed out his decade of hit films with The Apartment, a culmination of his many skills and strengths as a director. The film represents the apex of his filmmaking career, winning Oscars for Best Director (his second) and Best Picture. Wilder reteamed with Jack Lemon in this dramedy that follows CC Baxter, an ambitious Manhattan insurance clerk who loans out his apartment to married executives for private trysts, hoping they will remember him come promotion time. But complications ensue when Baxter tries to shut down his side hustle when he falls for Fran Kubelik (a charming Shirley MacLaine), a gamine-like elevator operator.
The Apartment’s racy plot clashed with the strict censorship codes of the time, but watching the film through today’s lens reveals a remarkable modern tone. Lemon and MacLaine share a charming chemistry that blends drama and comedy with a heavy dose of melancholy.
In an against-type performance, Fred MacMurray (best known as America’s Dad on the show My Three Sons) plays a sleazy CEO who relishes cheating on his doting family, forcing Baxter to face the moral failings of his ambition. The corporate drama that fuels the plot would influence such prestige dramas as Mad Men in tone and setting.
While there’s still fierce debate whether this or Sunset Boulevard is Wilder’s best film, both bookend a decade of influential filmmaking that few directors can rival. Sadly, the shifting landscape of Hollywood in the 1960s started Wilder’s slow decline as the industry’s most exciting director.
Kiss Me, Stupid (1964)
Wilder directed his first major flop with this crude farce, which featured the stunt casting of Rat Packer Dean Martin as a caricature of himself. Kiss Me, Stupid stars Ray Walston as Orville Spooner, a loser piano teacher in the Nevada town of (ahem) Climax, who hopes to sell a song to the famous crooner Dino (Martin), who’s stranded in town. To sweeten the deal, Orville sends his doting wife Zelda out for the night and hires bombshell prostitute Polly the Pistol to play his wife in the hopes she can sleep with the womanizing Dino.
Wilder developed Kiss Me Stupid as a vehicle for Peter Sellers and wrote the part of Polly for Marilyn Monroe. Unfortunately, Monroe's tragic death in 1962 derailed the project, and later, Sellers dropped out due to health issues. To replace Sellers the director brought in character actor Walston, who shows no leading man chops as Orville, losing the audience’s sympathy once his cynical scheming begins. Kim Novak fares no better as Polly the Pistol, doing a poor impersonation of Marilyn Monroe's lusty, naïve persona. The film springs to life whenever Martin appears on screen, as he’s having the time of his life playing an amorous version of his Vegas stage persona, constantly flirting whenever a pretty female crosses his sight.
Like The Apartment, Kiss Me Stupid’s racy plot rankled the censors of the time, causing a huge controversy upon release. The Legion of Decency condemned the picture, and the flop represents the nadir of Wilder’s career. Ironically, the sultry comedy might have fared better if released a few years later, as the classic censorship codes began to fade in the mid-1960s.
The Fortune Cookie (1966)
The director made quite the comeback when he paired Jack Lemmon and Walter Matthau for the first time in the classic comedy The Fortune Cookie. Lemmon and Matthau would become one of Hollywood’s great comedic duos, and The Fortune Cookie uses their magic chemistry to great effect. Lemmon stars as Harry Hinkle, a TV cameraman for NFL football who’s knocked unconscious on the field during a game. But his scheming lawyer brother-in-law Willie Gingrich (Matthau) convinces Harry to fake a severe injury to collect over a million in pain and suffering.
Matthau won a well-deserved Best Supporting Actor Oscar for his performance, and Wilder returned to form with this witty and clever caper. Matthau and Lemon would tag team in ten films, most famously in Neil Simon’s The Odd Couple in 1968. Modern audiences will recognize the duo’s Grumpy Old Men franchise in the 1990s. But The Fortune Cookie remains one of their best pairings due to Wilder’s cynical yet sweet script, highlighting Lemmon and Matthau’s combative chemistry.
The Front Page (1974)
Wilder would remake the classic 1931 comedy The Front Page as his penultimate film, reuniting the comedy duo of Jack Lemmon and Walter Matthau. The newspaper-set story chronicles ruthless editor Walter Burns (Matthau) scheming to get his top reporter, Hildy Johnson, to cover one last crime story before retirement. If this storyline sounds familiar, the same script served as the basis for the screwball classic His Girl Friday, changing the gender of Hildy to create a battle of the sexes between Rosalind Russell and Cary Grant.
Wilder refashioned the script to fit the singular Lemmon-Matthau chemistry, and the duo elevates the cliché tropes of the plot. This new version explored the darker elements of the original play that both the original 1931 film and His Girl Friday glossed over. Wilder reteamed with Lemmon and Matthau for his final movie Buddy Buddy in 1981, retiring from his long and influential filmmaking career.
