Once Upon a Time… in Hollywood begins with a clip from an old Western TV series called Bounty Law. Action star Rick Dalton plays Jake Cahill (no relation to the U.S. Marshal, J. D. Cahill) who’s a bounty hunter only out to make money for himself. The clip ends with an interview on NBC television with Rick and his stuntman, Cliff Booth. It’s Cliff’s job to carry Rick’s load. Wink wink. Nudge nudge.
Saturday, February 8th, 1969
We find Rick and Cliff at a restaurant where producer Marvin Schwarzs meets with Rick. He is a pretty big fan of Rick’s work, and he talks about having seen a double feature of him; one where he plays playing an action star, and another one where he is a GI that incinerates Nazis using a flamethrower. Marvin’s even seen his ultra cheesy music video he made.
Rick’s having trouble finding a steady acting gig since Bounty Law was canceled due to his alcoholism (whiskey sours will get you every time). Cliff is now also Rick’s driver because of his drinking problems. Rick had taken the part of the heavy on the TV series Lancer, but Schwarzs thinks Rick is doing himself a disservice by not flying out to Rome, and shoot some Spaghetti Westerns. Schwarzs’ blunt truths hits Rick hard, and he begins to cry. So Cliff gets him out of the restaurant ASAP. Rick tells Cliff that he’s now officially a has-been.
When Cliff drives Rick home, they find that Rick’s new neighbors are director Roman Polanski and his gorgeous wife, Sharon Tate (who’s been in a few movies of her own). Rick perks up a bit because he thinks the successful Rosemary’s Baby director can help him restart his career. That night, Cliff leaves Rick to rehearse his lines for Lancer while he drives to his little trailer where he lives alone with his pitbull Brandy.
Polanski takes Sharon to a party at the Playboy Mansion. There, they meet some friends: Jay Sebring, Steve McQueen, and Michelle Phillips. Sharon dances outside by the pool, while McQueen talks to Connie Stevens about how Sharon is playing Polanski to make Jay jealous, and that Jay knows it’s a matter of time until Polanski screws up, and Sharon will be his again. Connie says that Sharon has a type; short men that look like 12-year-old boys. Poor Steve never had a chance.
Sunday, February 9th, 1969
Once Polanski leaves the house, Jay stops by to hang out with Sharon. We see Charles Manson roaming outside, and when Jay confronts him, he claims he’s looking for his friends who are the home’s previous owners. No harm here. He apologizes and leaves.
That same morning, Cliff drives Rick to the set of Lancer for his first day’s shoot. As they arrive, Rick asks Cliff to fix the antenna on his roof as he didn’t get reception last night, so off Cliff goes. Manson has a friendly smile and a wave for Cliff as arrives on Rick’s street.
There’s a flashback where Rick talks to his old pal Randy who is the stunt coordinator for the film Rick was working on. He wants to get Cliff a job there. Randy’s very reluctant because there’s a rumor around town that Cliff murdered his wife, and since his own wife, Janet, believes Cliff got away with murder (and also since she’s working on the project too), he can’t hire him.
We next see the aforementioned incident on a boat where Cliff’s wife, Billie, nags Cliff to death. Cliff is holding a harpoon gun in a precarious position while pointed at her, but the scene cuts away before we learn if Cliff really shot Billie or not.
We cut back to Randy and Rick where Rick throws out the old “he’s a military veteran” card. Randy hires Cliff, and takes him to the set where Cliff soon finds himself listening to Bruce Lee talk about wanting to fight Cassius Clay. Cliff thinks he’s ridiculous, and laughs at him. This annoys Lee who challenges him to a fight to see who knocks whom to the ground first.
Lee knocks Cliff down first. Cliff gets up, grabs Lee, and tosses him into Janet’s car door. They then fight hand-to-hand until Janet interrupts the two; pissed that Cliff is fighting her star. The dent in her car just angers her more, and she fires Cliff on the spot, but Randy doesn’t like her doing that, so he then fires Cliff instead.
Back to Sharon who’s out and about to pick up a book as a gift to her hubby. She spots a local movie theater playing The Wrecking Crew which she has a role in. She goes to buy a ticket for it, but then stops and asks if she can see it for free since she’s a star in it.
When the manager comes over to the little box office, he recognizes Sharon from Valley of the Dolls, he then invites her in. As she sits and watches her film, Sharon intently watches, reenacts little fighting poses in her seat, and waits to hear people laughing and cheering at the right moments.
Meanwhile, Rick’s on a lunch break on the set of Lancer. On a quiet side-street of the lot, he comes across his eight-year-old co-star Trudi, a method actor, as she silently reads a book about Disney. Rick smokes a cigarette, and then asks if he can read his book next to her. The two talk about the books they are reading, but as Rick tells Trudi about the book he’s reading, the protagonist’s decline in life hits a bit too close to home. He breaks down crying.
Lunch is soon over, and shooting begins. Rick has a scene with the series’ lead actor, James Stacey who plays Johnny Madrid. Rick’s once again drinking which causes him to forget some of his lines. When he returns to his trailer, and has a meltdown over his shitty performance. He starts to take a swig of whiskey again, but throws it into the wall, and vows to do a better job.
With the antennae fixed, Cliff drives home from Rick’s place. On a street corner, he spots a hitchhiker named Pussycat that seems to be hitchhiking everywhere he’s been near over the past weekend. Since he’s headed the same way she’s pointing her thumb this time, he stops to pick her up. They chat, and he agrees to take her to Spahn Ranch where she lives with some others. Coincidentally, that ranch is where Rick and Cliff used to shoot films about eight years prior.
As they drive up, Cliff notices that the place is now some hippie commune made up of mostly teen girls and women. Pussycat wants Cliff to wait around to meet Charlie, but instead, Cliff wants to meet his old friend, George Spahn, the ranch’s elderly owner.
The girls tell Cliff that George is sleeping, but Cliff wants to talk to him anyway. He walks up to George’s house, but Lynette “Squeaky” Fromme won’t let him in because he’s sleeping after she fucked his brains out.
Cliff forces his way to George’s bedroom, but once there, George doesn’t have a clue who Cliff is since he’s blind. Cliff wants to know if the women are taking advantage of him, which George denies, and he tells Cliff to beat it.
Back out side, the female hippies jeer Cliff as he walks back to his car. When he gets to it, he finds a knife in the front driver’s side tire, and it’s flat. He takes the car jack out, and throws it down on the ground. He tells the male hippie who flattened it to fix it. The kid replies, “Fuck you!” so Cliff punches him squarely in the face three times in front of the women and girls there. The punk changes the tire while one of the girls rides away to tell Tex Watson of the trouble at the ranch. When Tex arrives, Cliff is already driving away.
We are back on the set of Lancer, and Rick shoots a scene where Trudi’s character is his hostage, and Scott Lancer is there to intervene. Rick improvises in the scene, and throws throws Trudi off of him to the ground. After the take, both both the director and Trudi highly praise his work. Trudi even says the Rick’s performance was the best acting she has ever seen in her life. Once again, Rick starts crying.
Six months later
Via a voice-over from Randy says that Rick took the offer to film some Spaghetti Westerns in Rome. Cliff came along for the ride. While there, Rick marries his Italian film actress co-star, Francesca Capucci.
August 8th, 1969
Rick and Cliff return to Los Angeles after making four feature films. However, Rick can not pay Cliff for his work any longer AND pay for his new wife when he’s having trouble even paying for himself. Therefore, it’s time for them to go their separate ways. When friends as close as brothers part, one last night drinking is in order. The men hit the town before crashing for the night at Rick’s home where Francesca suffers from jet lag.
Meanwhile next door, a very pregnant Sharon Tate has a little get together with Jay, and their friends Wojciech Frykowski and Abigail Folger.
Cliff takes out the acid-laced cigarette he bought from Pussycat for 50 cents, smokes it, and takes his dog for a walk outside. Tex rolls up in his clunker of a station wagon with fellow Manson family members Katie, Sadie, and Flowerchild. They have orders to kill Sharon and her friends. However, Tex’s muffler is broken, and it’s making too much noise at midnight. A pissed off and drunk Rick comes out to scream at them for the noise. He tells those hippies to beat it before he calls the cops.
Tex agrees to leave, throws the car in reverse, and then drives down the hill. Once at the bottom, the girls recognize Rick from TV. Sadie suggests that they kill him and anyone else in his house. They agree, but as they start walking back up the hill, Flowerchild claims to have forgotten her knife. Tex locked the doors, so he gives her the car keys. She goes to it, but drives away instead. The remaining three then carry on to kill Rick.
Tex and Katie break in through the front, while Sadie goes in through the side. By now, Cliff is back from his walk. When he sees them he doesn’t know if they are real or not because that cigarette he smoked is causing him to trip balls.
Tex pulls a gun on Cliff, but that acid has removed any fear he might have. He whistles to his dog Brandy who attacks Tex in the groin. When Sadie tries to run up to Cliff with her knife, he punches her in the face, and then has Brandy attack her. Cliff stomps Tex’s face until Katie takes her knife and stabs him in his right hip. Cliff gets up, and brutally begins smashing her face repeatedly against the fireplace mantle and phone and anything else he can find until she is dead.
Meanwhile, Sadie gets up, and stumbles outside into the pool. Rick’s been quietly lounging in it with some headphones on, and her crazed manner scares him. He goes to his shed, and pulls out the Flamethrower from the Nazi film he made years ago; burning the girl to death in his pool.
Both the paramedics and the police soon arrive. After some statements to the cops, the paramedics take Cliff to the hospital. Rick wants to come along, but Cliff want him to visit him in the morning instead. Francesca, who is completely freaked out, is asleep after taking five sleeping pills. Brandy followed her there to cuddle.
Once Rick says goodbye to Cliff in the ambulance, he spots Jay from Sharon’s gate. He calls Rick over, and Rick explains what happened. Jay reveals that he knows who Rick is, and he’s been teasing Sharon about her neighbor for sometime now. Sharon calls on her gate’s intercom, and she invites Rick to join them for a drink. Rick finally gets to meet Sharon and it looks like he may be able to one day schmooze Polanski for his next job.