There are few things Hollywood loves to spotlight more than itself. The era’s golden age boasts many films of the “let’s put on a show” variety filled with young ingenues realizing their dreams of superstardom. Who can forget Debbie Reynolds and Gene Kelley in Singin’ in the Rain embracing in front of a giant billboard for their next big screen hit?
As the industry matured over the next few decades, filmmakers started to show the dark side of Hollywood dreams, often filled with greed, carnal instinct, oversized egos, madness, and even murder. For every successful story, thousands upon thousands of dreamers fail in their pursuit of fame and fortune.
The following films explore the flip side of the patented Hollywood ending filled with cynical, hardened characters driven to extremes by the industry they love. Meet the dark side of Hollywood.
Sunset Boulevard (1950)
Director Billy Wilder’s operatic film noir remains the gold standard of dark Hollywood tales. While most modern audiences know the story through Andrew Lloyd Webber’s musical adaptation, the original Sunset Boulevard film still packs quite a punch. Wilder’s brilliant screenplay, co-written with Charles Brackett and D.M. Marshman Jr, imbues the tragic tale of faded film star Norma Desmond clinging desperately to her past glory with a cynical, if loving touch.
Sunset Boulevard features one of the great stunt castings in film history when Wilder cast former silent screen siren Gloria Swanson to play Norma Desmond. Swanson inhabits Norma by adding a meta layer to the performance, as Swanson herself walked away from the industry during the talkie transition and was desperate for a career comeback. Her exaggerated facial expressions and hand movements create a creepy, surreal atmosphere. And watching Norma’s final descent down the grand staircase, her arms outstretched, she resembles a spider trapped in a web of madness and deceit. Few movies look so unflinchingly into the dark side of Hollywood.
Whatever Happened to Baby Jane? (1962)
If Psycho was the grandfather of the slasher film, then Whatever Happened to Baby Jane is the genre’s grandmother. The horror movie plays like the spiritual sister to Sunset Boulevard, as it explores former child star Baby Jane Hudson as she clings to her past fame by tormenting her more talented sister Blanche, now a wheelchair-bound paraplegic. And much like Sunset Boulevard, the dark side of Hollywood picture features powerhouse meta-laced performances by legendary icons Bette Davis and Joan Crawford.
Sadly, the real-life backstage drama between Davis and Crawford has overshadowed this bleak and frightening movie. The legendary feud between the two divas is the stuff of Hollywood legend and even inspired the excellent 2017 FX mini-series Feud: Bette & Joan. And while both actors do fantastic work, Davis walks away with the picture. Her grotesque caricature of Baby Jane Hudson, with blonde curls and pounds of makeup, is a monster that could only be bred in the warped hills of Hollywood.
Babylon (2022)
2022’s opulent exploration of the early days of silent cinema’s rocky transition into talking pictures proved an expensive misfire. Director Damien Chazelle channels his inner Baz Luhrmann in this overlong and over-indulgent film. Stacked with an impressive cast led by Brad Pitt and Margot Robbie, Babylon paints a tapestry of storylines and characters as they navigate a shifting industry once The Jazz Singer heralds the arrival of the talkies.
Despite its flaws, Babylon effectively portrays the Wild West and anything-goes mentality of the early days of filmmaking. Silent cinema transformed actors into demi-god figures that filled the screen with mystery and romance. All that evaporated with talking pictures, as these larger-than-life idols were cut down to size by naturalistic dialogue that demanded real acting talent.
Tragedy strikes Pitt’s matinee idol and Robbie’s young starlet as they watch their once-promising careers implode. While the amped-up film shifts tone scene by scene, it expertly shows how the studio system extinguished the flame of wild creativity that was the hallmark of the silent age of Hollywood.
A Star Is Born (1954)
Hollywood has made four versions of the classic tale of a young ingenue whose fame eclipses that of her more seasoned celebrity lover. Each iteration reflects the persona of its leading ladies like Janet Gaynor, Barbra Streisand, and Lady Gaga. But the 1954 A Star is Born, starring Judy Garland, is the most well-known, thanks to its classic Gershwin-composed soundtrack.
Garland gives a career-defining performance as Vicki Lester, a singer/actress who rises through the ranks of Hollywood as she falls in love with movie star Norman Maine (James Mason), an alcoholic whose career is on the decline. The movie is a snapshot of the classic studio system and all the pain and rigor within the dark side of Hollywood.
While the film explores dark territory, Garland radiates classic movie star charisma. Her performance of “The Man That Got Away” is hands down her finest movie moment.
S1m0ne (2002)
Twenty years ago, filmmaker Andrew Niccol prophesized the coming of artificial intelligence and its effects on the entertainment industry with the criminally underseen S1mOne. Headlined by Al Pacino, the title stands for “Simulation One,” as it chronicles an auteur director who digitally creates an actress to replace the temperamental star who quit his film. But comedy ensues when the digital avatar becomes an overnight sensation that audiences and the hungry press think is a real person. It’s essentially a digital update of My Fair Lady, with director Niccol poking fun at the Hollywood studio system.
Niccol initially planned to create his Simone via CGI, but in 2002, the technology hadn’t matured enough to make a convincing human replica. Instead, he cast model/actress Rachel Roberts in the title role, giving her persona a digital gloss.
The movie explores A.I. themes that were way ahead of its time, and today, it’s a polarizing, if prescient, watch. Some twenty-two years later, the twin SAG-AFTRA and WGA strikes brought the industry to its knees, and one of the main sticking points was the rampant use of AI-created digital replicas. At the time, S1mOne played as a satirical comedy; now, it’s a warning of a future headed our way.
The Bad and the Beautiful (1952)
Just a few years after Sunset Boulevard, MGM released its movie that painted Hollywood in a darker light. The Bad and the Beautiful stars Kirk Douglas and Lana Turner in the story of Jonathan Shields, an unscrupulous movie producer who uses an actress, director, and writer to achieve success. When the trio gets called back to help Shields by working on his next feature, they recount their experiences working with the temperamental producer, who ironically helped launch their careers.
While the film features the standard MGM glamour, the story explores the struggles of the movie industry from the vantage point of the actor, writer, and director. While the entire cast gives strong performances, Lana Turner stands out. The bombshell beauty proved she was a legitimate actress by playing a young starlet struggling with alcoholism as she achieves success. It’s a film that shows the hustle of Hollywood can work both ways.
The Player (1992)
Director Robert Altman made a dramatic comeback with this razor-sharp satire of the Hollywood studio system. Tim Robbins stars as studio executive Griffin Mill, who starts to receive death threats from a rejected screenwriter. But which one, as Mill hears dozens of pitches each day? The Player features hilarious meta gags, like a character talking about cinema’s great tracking shots as the film opens with an unbroken 8-minute take. Or when Mill meets his colleagues for lunch and suggests they talk about something other than Hollywood, causing the table to erupt into laughter.
The Player captures an era in Hollywood before the studios were swallowed by mega-corporations, and intellectual property determined which movies were made. The late 80s and early 90s had executives listening to prospective pitches from writers for that next big idea. Director Alman also assembles a smorgasbord of celebrity cameos, like Cher, Burt Reynolds, Bruce Willis, Julia Roberts, and many more, all poking fun at the industry that made them stars.
The Black Dahlia (2006)
One of the great unsolved murder mysteries in Hollywood history remains the gruesome killing of hopeful actress Elizabeth Short, a case that was dubbed “The Black Dahlia.” Acclaimed director Brian De Palma adapted James Ellroy’s 1987 novel of the same name into a flawed, if compelling, recreation of the circumstances that led to Short’s demise. The film stars Josh Hartnett and Aaron Eckhart as two detectives assigned to the case. But as they uncover more clues and enter the mind of the would-be killer, the detectives find their professional and personal lives falling apart.
Ellroy stated that his novel was a loose interpretation of the Black Dahlia case, and his theories behind the mystery killer make for an entertaining thriller. De Palma crafts a creepy atmosphere and lenses The Black Dahlia like a 1940s version of Jack the Ripper. Yet the movie never forgets the tragic story of Elizabeth Short, the real-life actress filled with big dreams who came face to face with the dark side of Hollywood.
The Last Tycoon (1976 & 2016)
Literary giant F. Scott Fitzgerald, the author behind The Great Gatsby, famously worked in Hollywood as a screenwriter in 1927. But after toiling at MGM for eighteen months, he decided his writing talent didn’t translate to the cinema and called it quits. He dramatized his experience in his final, incomplete 1941 novel, The Last Tycoon, published posthumously after his death. The story tells the tale of Monroe Stahr, a young movie producer, and the power struggle with his mentor Pat Brady over their successful movie studio. Both Stahr and Brady were stand-ins for real-life legends Irving Thalberg and Louis B. Mayer, who ran MGM in the 1920s.
In 1976, legendary and controversial filmmaker Elia Kazan directed a big-budget adaptation of The Last Tycoon, which would become his final film. The picture stars a young, dapper Robert DeNiro as Stahr and Robert Mitchum as Brady. While the movie has the great acting you would expect from DeNiro and stately direction from Kazan, the film was met with mixed reactions from critics and audiences.
Amazon Prime’s lavish and forgotten 2016 TV version remains the superior adaption. A dashing Matt Bomer headlines The Last Tycoon, which perfectly recreates the dream factory kingdom of 1930s MGM in minute detail. With Kelsey Grammar as an imposing Brady, the series captures Fitzgerald’s emotionally charged tale of the backstage drama that fueled MGM’s rise to power.
Inside Daisy Clover (1965)
Natalie Wood completed her transformation from child star to adult actress in this dark fable on the cruelty of Hollywood. Inside Daisy Clover explores the push and pull between the actor and the studio star-making machine that embodies the dark side of Hollywood.
Wood stars as Daisy, a wild tomboy plucked from obscurity and remade into a teen superstar for the imposing Swan Studios. The film plays like an inversion of A Star is Born, with Daisy ultimately deciding to walk away from her newfound fame to regain control of her life.
Inside Daisy Clover paints an unflattering picture of 1930s Hollywood with a cold and nihilistic tone that portrays the classic studio system as a prison for actors. The film boasts an impressive cast, including a young Robert Redford as a male heartthrob who romances Daisy and Roddy McDowall, going against type as a cruel assistant.
Who Framed Roger Rabbit? (1988)
Wait, how did a Disney movie end up on this list? Yet this quirky and groundbreaking mash-up of animation and live-action features an undercurrent of the dark side of Hollywood.
At its core, Who Framed Roger Rabbit plays like a comedic variation of the classic film noir, filled with animated variations of noir cliches like zoot suit-dressed henchmen and Jessica Rabbit as the ultimate femme fatale. Bob Hoskins headlines this wacky caper of a toon-hating P.I. who unwittingly helps cartoon superstar Roger Rabbit prove his innocence after he’s framed for murder.
Who Framed Roger Rabbit used groundbreaking technical wizardry to blend animation and live action in stunning detail that still impresses 30 years after its release. But even more impressive was the cross-studio collaboration with Warner Bros and MGM that allowed Disney to use their animated characters, creating a fully realized toon universe (as long as they shared equal screen time with their Disney counterparts). It’s safe to say that this is the only film to feature a piano face-off between Daffy and Donald Duck.
The Day of the Locust (1975)
John Schlesinger directed this forgotten movie gem, adapting Nathaniel West’s acclaimed novel to the screen. Schlesinger applies the grit and grime from his previous masterpiece, Midnight Cowboy, to 1930s Hollywood and explores the dark side of Hollywood.
The Day of the Locust follows an art director who falls for a self-destructive young starlet as he helps her achieve her acting dreams. Yet this road to stardom will end in tragedy and savage violence.
The Day of the Locust perfectly captures the novel’s blistering indictment of the sham of Hollywood, portraying L.A. as a sun-drenched nightmare. Damien Chazelle’s more recent Babylon explores similar territory, filled with excessive characters that feel right at home in this version of Hollywood.
L.A. Confidential (1997)
The neo-noir adaptation of James Ellroy’s acclaimed novel became an instant classic upon its release, earning favorable comparisons to Chinatown.
While the sprawling labyrinth plot doesn’t focus entirely on the dark side of Hollywood, the industry rests in its crosshairs. L.A. Confidential chronicles the investigation of a gruesome mass murder at a local diner by three police detectives, where they uncover a trail of police corruption and Hollywood sleaze. The film features an impressive array of actors, including Guy Pearce, Kim Basinger, Kevin Spacey, James Cromwell, and Russell Crowe in his star-making turn.
One of the many subplots focuses on a ring of prostitutes who undergo plastic surgery to look like movie stars. In her haunted, Oscar-winning performance, Basinger embodies the sad fate of many Hollywood hopefuls with big dreams that ended in a nightmare. In this male-dominated film, Basinger’s Lynn Bracken, cut to resemble Veronica Lake, symbolizes Los Angeles in its tragic beauty.