The film opens with a clip from an old Western TV series, “Bounty Law”. It features action star Rick Dalton (Leonardo DiCaprio) in the lead role as Jake Cahill, a renegade bounty hunter. Following the clip is an interview with Rick and his stuntman, Cliff Booth (Brad Pitt), both of whom describe Cliff’s role as essentially carrying Rick’s load.
Saturday, February 8th, 1969 – Rick and Cliff are in a restaurant where Rick is met by producer Marvin Schwarz (Al Pacino). He is a fan of Rick’s work, having seen a double feature presentation of his where he plays an action star, including one where he is a GI that incinerates nazis with a flamethrower (which he kept). Marvin also brings up a cheesy music video Rick was featured in. “Bounty Law” has since been canceled because of Rick’s ongoing alcoholism (which is also why Cliff is his driver), and now Rick has booked a gig as a villain on the series “Lancer.” Marvin thinks Rick ought to fly to Rome and shoot Spaghetti Westerns. Rick complains to Cliff about how this means that his career is going downhill, and he is now a has-been.
Cliff drives Rick home, where they learn that Rick’s new neighbors are director Roman Polanski (Rafal Zawierucha) and his wife, rising starlet Sharon Tate (Margot Robbie). Rick’s mood turns around since he thinks that a big time director like Polanski (hot off “Rosemary’s Baby”) can help reinvigorate his career. He goes to rehearse his lines for “Lancer” for the night. Cliff then drives home to his trailer where he lives alone with his dog Brandy.
Polanski brings Sharon to a party at the Playboy Mansion, where they meet with their friends Jay Sebring (Emile Hirsch), Steve McQueen (Damien Lewis), and Michelle Phillips (Rebecca Rittenhouse). Sharon goes to dance, while McQueen talks to Connie Stevens (Dreama Walker). He notes that Sharon is using Polanski to make Jay jealous, and Connie thinks that Sharon has a type – short men that “look like 12-year-old boys”.
Sunday, February 9th, 1969 – After Polanski leaves, Sharon hangs out with Jay at her house. Visiting them is Charles Manson (Damon Herriman), claiming that he is coming to see his friends, the previous owners of the house that Polanski and Sharon now live in. He apologizes for the error and leaves.
Cliff brings Rick to the set of “Lancer” for the day’s shoot. He goes back to Rick’s house after he asks Cliff to fix the antenna on his roof. He happens to spot Manson as he leaves, and he smiles and waves at Cliff. We then see a flashback to Rick talking to an old friend of his, Randy (Kurt Russell), into getting Cliff a gig. Randy shows reluctance, since it is rumored that Cliff murdered his wife Billie (Rebecca Gayheart) and got away with it. The alleged incident is shown on a boat where Billie was nagging Cliff endlessly, but it cuts away before we see if Cliff really did shoot Billie with the harpoon gun he was holding. Randy brings Cliff to the set, where he meets Bruce Lee (Mike Moh) talking about wanting to fight Muhammad Ali. When Lee catches Cliff laughing at what he’s saying, he challenges him to a fight to see who knocks who on the ground first. Lee gets Cliff down first, and he retaliates by grabbing Lee and slamming him into a car. The two then go hand-to-hand until Janet (Zoe Bell), Randy’s wife and fellow stunt coordinator comes in and is pissed to see Cliff and Lee fighting, and the huge dent that Cliff left in there, meaning he’s fired.
Sharon goes to the local movie theater and sees that a film she is featured in, “The Wrecking Crew”, is playing. She goes to the box office and asks for a ticket, but then asks if she gets any privilege for starring in the film. The manager comes out and recognizes Sharon from “Valley of the Dolls”, and he invites her in. Throughout the film, Sharon listens to the audience’s enthusiastic reactions to her performance, with laughter and cheering at the right moments.
Rick goes through his hair and make-up for “Lancer”. He then sits down next to his eight-year-old co-star Trudi (Julia Butters), who is a method actor. Rick smokes a cigarette near her as she reads her book. They have a conversation about the books they are reading, and Rick has a small breakdown over his perceived decline in stardom. Shooting begins, and Rick works with the series’ lead actor, James Stacey (Timothy Olyphant), who plays protagonist Johnny Madrid. During the take, Rick forgets his lines due to being drunk. He goes to his trailer and has a meltdown, but then vows to do better.
Cliff drives home from Rick’s place and sees a hitchhiker called Pussycat (Margaret Qualley), whom Cliff has noticed throughout the weekend. He picks her up and agrees to take her to the Spahn Ranch, where Cliff used to shoot films with Rick. When they get there, Cliff sees that the place has become some kind of commune for hippies, mostly consisting of women. Pussycat tells Cliff that he should stick around to meet Manson, but he wants to speak with the ranch’s owner, George Spahn (Bruce Dern). The women warn Cliff that Spahn is sleeping, but he goes over to his house anyway. He is met by Lynette “Squeaky” Fromme (Dakota Fanning), who also reiterates that Spahn is asleep because she just had sex with him. Cliff goes to wake Spahn up, but he doesn’t recognize Cliff since he is blind. He asks Spahn if the women there are taking advantage of him, but Spahn denies it and tells Cliff to leave. Outside, Cliff sees one of the male hippie’s stuck a knife in his front tire. He gets his stuff out and orders the man to fix it, but is given a “fuck you”. Cliff responds by decking the guy hard in the face three times in front of the other women. They run to get Tex Watson (Austin Butler), but Cliff is already driving away by the time he gets out.
Back on the “Lancer” set, Rick shoots a scene where he has Trudi’s character hostage, and Scott Lancer, played by Wayne Maunder (Luke Perry), comes to intervene. Rick improvises his slimy villain character and has a moment where he throws Trudi off of him. After the take, he is praised by both the director and Trudi, who tells Rick that it was the best acting she has ever seen in her life. The comment even moves Rick to tears.
We then jump to six months later. A voiceover from Randy states that Rick and Cliff ended up flying to Rome to shoot the Spaghetti Western films. While there, Rick met and married Italian film actress Francesca Capucci (Lorenza Izzo).
August 8th, 1969 – Rick and Cliff have returned to Los Angeles, but now feel that it is time for them to go their separate ways. They spend one last night having drinks and hang out at Rick’s home with Francesca. Meanwhile, Sharon, now very pregnant, is having a small gathering with Jay, and their friends Wojciech Frykowski (Costa Ronin) and Abigail Folger (Samantha Robinson).
Cliff takes out a cigarette he bought from Pussycat that was dipped in acid, and he proceeds to smoke it to trip out. Outside, Tex drives in front of the houses with fellow “family” members Patricia Krenwinkel, AKA Katie (Madisen Beaty), Susan Atkins, AKA Sadie (Mikey Madison), and Linda Kasabian, AKA Flowerchild (Maya Hawke). They arrive with the intention of killing Sharon and her friends, but a drunk Rick comes out and angrily yells at them because their car’s busted muffler is making too much noise. He orders them to leave, even as Katie appears to be reaching for her gun, but Tex drives away. At the bottom of the hill, the four recognize Rick from TV, and Sadie suggests that they kill him and whoever else is in his house. The others agree, but as they start walking there, Flowerchild says she forgot her knife. Tex gives her the car keys to get it, but she ends up ditching them and driving away. The three then proceed to carry out their plan.
The trio walk up to Rick’s house. Tex and Katie break in through the front, while Sadie goes in through the side. Cliff sees them, but because he is tripping balls, he is neither frightened nor absolutely certain of what he is seeing. Even as Tex draws his gun on Cliff, he instead sics Brandy on Tex, who viciously chomps into Tex’s arm and groin. Sadie tries to run up to Cliff with her knife, but he chucks a can of dog food at her, which smashes into her face. Cliff stomps Tex’s face in before grabbing Sadie and brutally smashing her face against the hard furniture until she is dead. Brandy gets a few bites into Sadie as well, but she runs out flailing and shrieking into the pool, where Rick is lounging. He then comes out with his FLAMETHROWER and torches Sadie, who burns to death in his pool. In the chaos, Cliff gets shot, but non-fatally.
Paramedics and police arrive at the scene. Cliff is taken to the hospital for his injuries, while Francesca is freaked out by the ordeal. After Rick says bye to Cliff, he sees Jay calling to him from Sharon’s gate. Rick explains what happened, and Jay recognizes Rick from TV. Jay tells Sharon who her neighbor is, and they invite him to come over for a drink. Rick agrees, and he finally meets Sharon and her friends.
