Best Movies like Once Upon a Time… in Hollywood (2019)

Boogie Nights and Once Upon a Time... in Hollywood both explore the shifting landscape of Los Angeles’ entertainment world during the late 20th century, tracing the rise and fall of showbiz hopefuls as they are swept up in the glamour, challenges, and changing dynamics of fame and popular culture.

In 1977, an idealistic porn producer and his promising protege try to catch up with the end of an era before their never-ending party collides with cold, hard reality. Boogie Nights is a movie from United States of America in English, with a total 2h 36m runtime, released in 1997 with an average rating of 7.6 by 3,627 people. The movie made an estimated total of $43,101,594 in the box office.

Inherent Vice is set in California during a period of social upheaval, much like Once Upon a Time... in Hollywood’s late-1960s backdrop, capturing eccentric characters navigating Los Angeles’ strange mix of counterculture, crime, and nostalgia for a fading era.

In Los Angeles at the turn of the 1970s, drug-fueled detective Larry "Doc" Sportello investigates the disappearance of an ex-girlfriend. Inherent Vice is a movie from United States of America in English, with a total 2h 29m runtime, released in 2014 with an average rating of 6.5 by 2,747 people. The movie made an estimated total of $14,810,975 in the box office.

The Nice Guys unravels a quirky crime story featuring unlikely partners in 1970s Los Angeles—a period of transition and eccentricity, reflecting the vintage Hollywood vibe and setting found in Once Upon a Time... in Hollywood.

A private eye investigates the apparent suicide of a fading porn star in 1970s Los Angeles and uncovers a conspiracy. The Nice Guys is a movie from United States of America in English, with a total 1h 56m runtime, released in 2016 with an average rating of 7.1 by 8,791 people. The movie made an estimated total of $71,261,763 in the box office.

Hail, Caesar! draws audiences behind the scenes of classic Hollywood, focusing on the film industry’s inner workings through period detail, nods to stardom, and the unique pressures facing actors and creators, echoing the themes of showbiz uncertainty present in Once Upon a Time... in Hollywood.

When a Hollywood star mysteriously disappears in the middle of filming, the studio sends their fixer to get him back. Hail, Caesar! is a movie from United States of America in English, with a total 1h 46m runtime, released in 2016 with an average rating of 5.9 by 4,041 people. The movie made an estimated total of $63,647,656 in the box office.

The Player centers on the moral ambiguities and shifting fortunes within Hollywood’s movie business, examining characters whose livelihoods are threatened by industry changes, paralleling the anxious transition and self-examination faced by actors in Once Upon a Time... in Hollywood.

A Hollywood studio executive is being sent death threats by a writer whose script he rejected - but which one? The Player is a movie from United States of America in English, with a total 2h 4m runtime, released in 1992 with an average rating of 7.2 by 964 people. The movie made an estimated total of $21,706,101 in the box office.

Sunset Boulevard depicts the darkly glamorous world of aging Hollywood stars grappling with obsolescence and shifting celebrity, offering a sharp commentary on the cost of fame and reinvention that mirrors the struggles of actors in Once Upon a Time... in Hollywood.

A hack screenwriter writes a screenplay for a former silent film star who has faded into Hollywood obscurity. Sunset Boulevard is a movie from United States of America in English, with a total 1h 50m runtime, released in 1950 with an average rating of 8.3 by 2,975 people. The movie made an estimated total of $5,000,000 in the box office.

L.A. Confidential offers an exploration of crime and corruption within the glitzy 1950s Los Angeles, providing a noir perspective on Hollywood’s murky underbelly—a thematic echo of Once Upon a Time... in Hollywood’s intersection of entertainment and danger.

Three detectives in the corrupt and brutal L.A. police force of the 1950s use differing methods to uncover a conspiracy behind the shotgun slayings of the patrons at an all-night diner. L.A. Confidential is a movie from United States of America in English, with a total 2h 18m runtime, released in 1997 with an average rating of 7.8 by 5,634 people. The movie made an estimated total of $126,216,940 in the box office.

Ed Wood celebrates the passion and resilience of struggling filmmakers in mid-century Hollywood, vividly portraying industry outsiders fighting for creative relevance, similar to the emotional and professional uncertainties experienced by characters in Once Upon a Time... in Hollywood.

The mostly true story of the legendary "worst director of all time", who, with the help of his strange friends, filmed countless B-movies without ever becoming famous or successful. Ed Wood is a movie from United States of America in English, with a total 2h 7m runtime, released in 1994 with an average rating of 7.5 by 2,549 people. The movie made an estimated total of $5,900,000 in the box office.

Mulholland Drive examines the allure and peril of the Los Angeles film scene, weaving together ambition, identity, and surreal twists—mirroring Once Upon a Time... in Hollywood’s fascination with Hollywood dreams and the shadowy edges of star-making.

Blonde Betty Elms has only just arrived in Hollywood to become a movie star when she meets an enigmatic brunette with amnesia. Meanwhile, as the two set off to solve the second woman's identity, filmmaker Adam Kesher runs into ominous trouble while casting his latest project. Mulholland Drive is a movie from United States of America in English, with a total 2h 27m runtime, released in 2001 with an average rating of 7.8 by 7,155 people. The movie made an estimated total of $20,289,986 in the box office.

Barton Fink delves into a writer’s experience within the film industry, probing Hollywood’s impact on creativity and personal identity, resonating with themes of artistic struggle and bewilderment amid shifting industry norms seen in Once Upon a Time... in Hollywood.

A renowned New York playwright is enticed to California to write for the movies and discovers the hellish truth of Hollywood. Barton Fink is a movie from United States of America in English, with a total 1h 57m runtime, released in 1991 with an average rating of 7.5 by 1,909 people. The movie made an estimated total of $6,153,939 in the box office.

Maps to the Stars explores the personal cost of chasing fame and relevance in Hollywood, dissecting the intersection of celebrity, ambition, and family dysfunction—territory similarly unsettled in Once Upon a Time... in Hollywood’s view of Tinseltown transformation.

Driven by an intense need for fame and validation, members of a dysfunctional Hollywood family chase celebrity, one another, and the relentless ghosts of their pasts. Their fragile ecosystem is disrupted by the arrival of Agatha, the scarred and estranged pyromaniac daughter. Maps to the Stars is a movie from Canada in English, with a total 1h 52m runtime, released in 2014 with an average rating of 6.2 by 1,156 people. The movie made an estimated total of $4,510,000 in the box office.

Hollywoodland investigates Hollywood’s mythmaking and the legacies of faded stars, drawing on the industry’s shifting fortunes and the challenges of lasting fame, which echoes the anxieties and shifting identities encountered in Once Upon a Time... in Hollywood.

When Hollywood superstar George Reeves dies in his home, private detective Louis Simo is hired to investigate his death and gets caught in a web of lies involving a big studio executive's wife. Based on a true story. Hollywoodland is a movie from United States of America in English, with a total 2h 6m runtime, released in 2006 with an average rating of 6.1 by 457 people. The movie made an estimated total of $16,803,753 in the box office.

The Big Lebowski is set against the backdrop of Los Angeles, blending offbeat humor with subcultures and fringe characters. Both films evoke a playful navigation through the idiosyncratic world of LA, throwing ordinary figures into extraordinary circumstances within the city’s unique ecosystem.

Jeffrey 'The Dude' Lebowski, a Los Angeles slacker who only wants to bowl and drink White Russians, is mistaken for another Jeffrey Lebowski, a wheelchair-bound millionaire, and finds himself dragged into a strange series of events involving nihilists, adult film producers, ferrets, errant toes, and large sums of money. The Big Lebowski is a movie from United States of America in English, with a total 1h 57m runtime, released in 1998 with an average rating of 7.8 by 12,344 people. The movie made an estimated total of $47,010,480 in the box office.

Café Society revisits vintage showbiz culture, spotlighting shifting romances and ambitions among people trying to find their place in mid-20th-century entertainment circles—a narrative kin to the personal quests and old Hollywood atmosphere of Once Upon a Time... in Hollywood.

The story of a young man who arrives in Hollywood during the 1930s hoping to work in the film industry, falls in love, and finds himself swept up in the vibrant café society that defined the spirit of the age. Café Society is a movie from United States of America in English, with a total 1h 37m runtime, released in 2016 with an average rating of 6.4 by 2,837 people. The movie made an estimated total of $43,763,247 in the box office.

Day for Night captures the camaraderie, chaos, and devotion behind filmmaking, delving into the hopes, disappointments, and everyday drama faced by those in the movie business, much like the insider’s lens on the Hollywood community portrayed in Once Upon a Time... in Hollywood.

A committed filmmaker struggles to complete his latest project while coping with a myriad of crises, personal and professional, among the cast and crew. Day for Night is a movie from France in French, with a total 1h 56m runtime, released in 1973 with an average rating of 7.8 by 666 people. The movie made an estimated total of $850,000 in the box office.

Somewhere shines a light on the private struggles and ennui of a celebrity in Los Angeles, using minimalist storytelling to explore identity and belonging—matching the existential uncertainties faced by actors and creators in Once Upon a Time... in Hollywood.

After withdrawing to the Chateau Marmont, a passionless Hollywood actor reexamines his life when his eleven-year-old daughter surprises him with a visit. Somewhere is a movie from United States of America in English, with a total 1h 38m runtime, released in 2010 with an average rating of 6.1 by 821 people. The movie made an estimated total of $14,788,642 in the box office.

The Long Goodbye explores Los Angeles through a vintage noir lens, following a protagonist drawn into a twisting landscape of crime and fading glamour. Both films reflect on the end of eras and enduring myths rooted in LA’s cultural milieu.

In 1970s Hollywood, Detective Philip Marlowe tries to help a friend who is accused of murdering his wife. The Long Goodbye is a movie from United States of America in English, with a total 1h 52m runtime, released in 1973 with an average rating of 7.4 by 785 people. The movie made an estimated total of $959,000 in the box office.

The Stunt Man focuses on the bizarre and dangerous world of film stunts, offering a perspective from the edge of Hollywood’s spotlight that aligns with Once Upon a Time... in Hollywood’s exploration of the unheralded but crucial figures who keep movie dreams alive.

A fugitive stumbles onto a movie set just when they need a new stunt man, takes the job as a way to hide out and falls for the leading lady while facing off with his manipulative director. The Stunt Man is a movie from United States of America in English, with a total 2h 11m runtime, released in 1980 with an average rating of 6.6 by 170 people.

The Last Tycoon traces the ambitions and insecurities of Hollywood’s creative minds during a transitional period, centering on the personal costs and power dynamics that come with adapting to change—a strong parallel to the industry’s evolution depicted in Once Upon a Time... in Hollywood.

Monroe Stahr, a successful movie producer, pursues a beautiful and elusive young woman — all the while working himself to death. The Last Tycoon is a movie from United States of America in English, with a total 2h 3m runtime, released in 1976 with an average rating of 6.3 by 165 people.

Tootsie follows an actor navigating the competitive, often absurd landscape of show business, spotlighting personal reinvention and the realities of showbiz careers—reminiscent of the adaptation and self-discovery seen in Once Upon a Time... in Hollywood.

When struggling, out of work actor Michael Dorsey secretly adopts a female alter ego—Dorothy Michaels—in order to land a part in a daytime drama, he unwittingly becomes a feminist icon and ends up in a romantic pickle. Tootsie is a movie from United States of America in English, with a total 1h 56m runtime, released in 1982 with an average rating of 7.2 by 1,950 people. The movie made an estimated total of $177,200,000 in the box office.

Starsky & Hutch, set in Los Angeles and riffing on classic TV-era entertainment, evokes the atmosphere of 1970s California, complementing Once Upon a Time... in Hollywood’s reimagining of showbiz and pop culture in the city’s past.

Join uptight David Starsky and laid-back Ken "Hutch" Hutchinson as they're paired for the first time as undercover cops. The new partners must overcome their differences to solve an important case with help from street informant Huggy Bear and persuasive criminal Reese Feldman. Starsky & Hutch is a movie from United States of America in English, with a total 1h 41m runtime, released in 2004 with an average rating of 5.8 by 2,556 people. The movie made an estimated total of $170,300,000 in the box office.

Irma Vep unpacks filmmaking’s creative process and the interplay between real life and performance on a movie set. It provides a behind-the-scenes glimpse at artistic ambition and chaos, relevant to Once Upon a Time... in Hollywood’s affection for film culture and those who make it.

A has-been French filmmaker wants a Hong Kong actress to be the heroine in a rendering of Les Vampires. Irma Vep is a movie from France in French, with a total 1h 39m runtime, released in 1996 with an average rating of 6.7 by 251 people.

S.O.B. lampoons the Hollywood filmmaking system and its excesses, unpacking the commercial and personal pressures that come with industry upheaval. Both S.O.B. and Once Upon a Time... in Hollywood scrutinize the unpredictable, changing face of movie stardom.

A movie producer who made a huge flop tries to salvage his career by revamping his film as an erotic production, where its family-friendly star takes her top off. S.O.B. is a movie from United States of America in English, with a total 2h 1m runtime, released in 1981 with an average rating of 6.0 by 99 people.

Get Shorty revolves around the collision between crime and the film business in Los Angeles, using sharp humor to explore how outsiders struggle to navigate and influence the entertainment industry, which echoes themes from Once Upon a Time... in Hollywood.

Chili Palmer is a Miami mobster who gets sent to L.A. to collect a bad debt from Harry Zimm, a Hollywood producer who specializes in cheesy horror films. When Chili meets Harry's leading lady, the romantic sparks fly. After pitching his own life story as a movie idea, Chili learns that being a mobster and being a Hollywood producer really aren't all that different. Get Shorty is a movie from United States of America in English, with a total 1h 45m runtime, released in 1995 with an average rating of 6.5 by 1,234 people. The movie made an estimated total of $115,101,622 in the box office.

Living in Oblivion humorously dissects the unpredictable trials of making an independent film, highlighting the behind-the-scenes chaos and dreams of show business hopefuls—a perspective on Hollywood’s backstage struggles that aligns with Once Upon a Time... in Hollywood.

Low-budget independent filmmaker Nick Reve tries to keep everything together as his production is plagued with an insecure actress, a megalomaniac star, a pretentious beret-wearing director of photography, and lousy catering. Living in Oblivion is a movie from United States of America in English, with a total 1h 30m runtime, released in 1995 with an average rating of 7.2 by 333 people. The movie made an estimated total of $1,148,752 in the box office.

Adaptation. explores the challenges of creative work within Hollywood, following artists’ battles with self-doubt and the convoluted realities of movie production. Like Once Upon a Time... in Hollywood, it examines how personal ambition and industry expectations intertwine.

Charlie Kaufman is a confused L.A. screenwriter overwhelmed by feelings of inadequacy, sexual frustration, self-loathing, and by the screenwriting ambitions of his freeloading twin brother Donald. While struggling to adapt "The Orchid Thief," by Susan Orlean, Kaufman's life spins from pathetic to bizarre. The lives of Kaufman and Orlean's book become strangely intertwined as each one's search for passion collides with the other's. Adaptation. is a movie from United States of America in English, with a total 1h 55m runtime, released in 2002 with an average rating of 7.3 by 2,820 people. The movie made an estimated total of $32,800,000 in the box office.

La La Land immerses viewers in the world of modern-day Los Angeles dreamers seeking artistic breakthroughs, echoing the ambitions, setbacks, and sentimental nostalgia for Hollywood’s golden age that frame the journeys of characters in Once Upon a Time... in Hollywood.

Mia, an aspiring actress, serves lattes to movie stars in between auditions and Sebastian, a jazz musician, scrapes by playing cocktail party gigs in dingy bars, but as success mounts they are faced with decisions that begin to fray the fragile fabric of their love affair, and the dreams they worked so hard to maintain in each other threaten to rip them apart. La La Land is a movie from United States of America in English, with a total 2h 9m runtime, released in 2016 with an average rating of 7.9 by 18,305 people. The movie made an estimated total of $509,183,536 in the box office.

Stardust Memories reflects on nostalgia, fame, and the bittersweet experience of creative work within show business—central themes for the characters navigating their own legacies in the transforming film industry of Once Upon a Time... in Hollywood.

While attending a retrospect of his work, a filmmaker recalls his life and his loves: the inspirations for his films. Stardust Memories is a movie from United States of America in English, with a total 1h 29m runtime, released in 1980 with an average rating of 6.9 by 468 people. The movie made an estimated total of $10,389,003 in the box office.

Swimming with Sharks spotlights the ruthless undercurrents of Hollywood’s business culture, providing a darkly comic take on the sacrifices and manipulations endured by those seeking success in the entertainment world—echoing the high-stakes pressures found in Once Upon a Time... in Hollywood.

Guy is a young film executive who's willing to do whatever it takes to make it in Hollywood. He begins working for famed producer Buddy Ackerman, a domineering, manipulative, coldhearted boss. When Guy also finds out that his cynical girlfriend, Dawn, has been using sex as a career move, he reaches his limit. Guy decides to exact revenge on Buddy by kidnapping him and subjecting him to cruel and unusual punishment. Swimming with Sharks is a movie from United States of America in English, with a total 1h 33m runtime, released in 1994 with an average rating of 6.6 by 339 people. The movie made an estimated total of $382,928 in the box office.

The Artist celebrates silent-era Hollywood, focusing on an actor’s career jeopardized by industry change. Both it and Once Upon a Time... in Hollywood chronicle personal and professional reinvention as show business moves inexorably forward.

Hollywood, 1927: As silent movie star George Valentin wonders if the arrival of talking pictures will cause him to fade into oblivion, he sparks with Peppy Miller, a young dancer set for a big break. The Artist is a movie from France in French, with a total 1h 40m runtime, released in 2011 with an average rating of 7.4 by 3,564 people. The movie made an estimated total of $133,432,856 in the box office.

Who Framed Roger Rabbit places real and animated characters in a film industry setting in Los Angeles, blending reverence for classic Hollywood style with playful genre subversion, similar to the inventive homage seen in Once Upon a Time... in Hollywood.

Toon star Roger is worried that his wife Jessica is playing pattycake with someone else, so the studio hires detective Eddie Valiant to snoop on her. But the stakes are quickly raised when Marvin Acme is found dead and Roger is the prime suspect. Who Framed Roger Rabbit is a movie from United States of America in English, with a total 1h 44m runtime, released in 1988 with an average rating of 7.5 by 6,266 people. The movie made an estimated total of $329,800,000 in the box office.

Singin' in the Rain explores the movie industry’s growing pains as it transitions from silent films to talkies, reflecting once-towering stars’ struggles to adapt—an arc reminiscent of the industry’s evolution and career uncertainty depicted in Once Upon a Time... in Hollywood.

In 1927 Hollywood, a silent film star falls for a chorus girl just as he and his paranoid screen partner struggle to make the difficult transition to talking pictures. Singin' in the Rain is a movie from United States of America in English, with a total 1h 43m runtime, released in 1952 with an average rating of 8.1 by 3,554 people. The movie made an estimated total of $7,200,000 in the box office.

A Star Is Born (1976) examines the triumphs and sacrifices intertwined with rising and fading stardom, resonating with the personal journeys and shifting fortunes of actors confronting a changing Hollywood in Once Upon a Time... in Hollywood.

Drunken, has-been rock star John Norman Howard falls in love with unknown singer Esther Hoffman after seeing her perform at a club. He lets her sing a few songs at one of his shows and she becomes the talk of the music industry. Esther's star begins to rise, while John's continues to fall. She tries desperately to get John to sober up and focus on his music, but it may be too late to save him. A Star Is Born is a movie from United States of America in English, with a total 2h 20m runtime, released in 1976 with an average rating of 6.0 by 243 people. The movie made an estimated total of $80,000,000 in the box office.

A Star Is Born (2018) traces the intersecting lives of performers grappling with success, reinvention, and the personal costs of fame. These themes closely mirror Once Upon a Time... in Hollywood’s portrayal of stardom in flux during key moments of cultural transition.

Seasoned musician Jackson Maine discovers — and falls in love with — struggling artist Ally. She has just about given up on her dream to make it big as a singer — until Jack coaxes her into the spotlight. But even as Ally's career takes off, the personal side of their relationship is breaking down, as Jack fights an ongoing battle with his own internal demons. A Star Is Born is a movie from United States of America in English, with a total 2h 16m runtime, released in 2018 with an average rating of 7.5 by 12,306 people. The movie made an estimated total of $436,388,866 in the box office.

The Day of the Locust explores the darker facets of Hollywood ambition and the lure of fame, depicting dreams unraveling during a tumultuous phase of industry transformation—elements that also define the character arcs and setting of Once Upon a Time... in Hollywood.

Hollywood, 1930s. Tod Hackett, a young painter who tries to make his way as an art director in the lurid world of film industry, gets infatuated with his neighbor Faye Greener, an aspiring actress who prefers the life that Homer Simpson, a lone accountant, can offer her. The Day of the Locust is a movie from United States of America in English, with a total 2h 25m runtime, released in 1975 with an average rating of 6.4 by 112 people.