Famous Age-Gap Relationships: Brad Pitt (24) and Shalane McCall (15) | Pitt (26) and Juliette Lewis (16)

Here's IMDb's plot summary for Once Upon a Time ... in Hollywood (2019):

A faded television actor [Rick Dalton (Leonardo DiCaprio)] and his stunt double [Cliff Booth] strive to achieve fame and success in the film industry during the final years of Hollywood's Golden Age in 1969 Los Angeles.

In the film, the infamous Manson Family played a bloody role. In one scene, Cliff, who was played by 56-year-old Brad Pitt, gave Pussycat (Margaret Qualley), an underage teen member of the Manson Family, a ride to the Spahn Ranch, which was where the Manson Family resided. 

During the ride, possibly as a means of paying her fare, Pussycat asked Cliff , “Want me to suck your cock while driving?” However, Cliff refused Pussycat’s offer, because he didn’t believe that she was, at least, 18. Thereby, Cliff implied that if Pussycat were, at least, 18, he would have allowed her to perform oral while he drove. Interestingly, Pussycat implied that, in general, men didn’t bother to inquire about her age. Here's the dialogue:

Pussycat, “Want me to suck your cock while driving?”

Cliff Booth, “How old are you?”

Pussycat, “What?”

Cliff Booth, “How old are you?”

Pussycat, “Wow, man. First time anybody asked that in a long time.”

Cliff Booth, “What's the answer?”

Pussycat, “Okay, we gonna play kiddie games? Eighteen. Feel better?”

Cliff Booth, “You got some I.D., you know, like, a driver's license or something?”

Pussycat, “Are you joking?”

Cliff Booth, “No, I'm not. I need to see something official that verifies that you're eighteen, which you don't have because you're not.”

Subsequently, in response to having her oral offered refused, Pussycat stated that she was not “too young to fuck” Cliff but that Cliff was “too old to fuck” her. 

Pussycat, “Obviously. I’m not too young to fuck you. But you’re too old to fuck me.”

Shalane McCall and Brad Pitt

In a double bit of art imitating life, back in 1987, 24-year-old Brad Pitt played Randy and 15-year-old Shalane McCall played Charlotte on the prime time soap opera Dallas, where Randy and Charlotte had an age-gap relationship in which they shared an age-gap kiss and love scene. 

In terms of the kiss, Charlotte had Randy over to her house while her parents were away, but to Charlotte’s dismay, her mother and Ray, her step-father, returned home a day early and, consequently, witnessed Charlotte and Randy kissing passionately.

Later, a furious Ray caught Charlotte and Randy making out on the floor of the barn, but Charlotte didn’t understand why Ray was furious, because, as she opined, they were just “fooling around”. 

Reportedly, McCall shared with People magazine (1988) that filming romantic scenes with Pitt (i.e., a much older man) wasn’t awkward. McCall reportedly shared:

“I met him an hour before shooting. But it wasn't awkward. We were laughing and kidding around.”

However, Cherie Holton, McCall’s mother, reportedly related to People that her daughter felt some “anxiety” about kissing Pitt, because McCall was inexperienced. Cherie Holton shared:

“I can tell you there was anxiety on Chellain's part. It's not cool at her age to admit how inexperienced you are. She's only kissed about three boys in her life.”

In the W Magazine piece “Brad Pitt Tries to Find the Music in Each Day” (Jan. 9, 2023), Pitt reminisced over his age-gap love scene with McCall, which he referred to as “frolicking” “in the hay in a barn”.

W Magazine: What was your first love scene?

Pitt: It would have been in the show Dallas. I had to roll around in the hay in a barn. I don’t think I had a line. I was just rolling and frolicking.

Juliette Lewis and Brad Pitt

Brad Pitt and Shalane McCall had an age-gap affair off-screen as well. They openly dated for about a year until, at the age of 17, McCall married the musician Trent Valladares. And in 1989, 26-year-old Pitt started dating 16-year-old Juliette Lewis. 

Amanda (Juliette Lewis) "Too Young to Die?"

Pitt and Lewis met on the set of Too Young to Die?. In the film, Lewis played Amanda, a 15-year-old sex worker, who had an age-gap relationship with her pimp Billy (Pitt) and with Mike (≈ 34-year-old Michael O'Keefe). 

Rain (Juliette Lewis) "Husbands and Wives"

Interestingly, a year before Lewis and Pitt ended their age-gap affair, Lewis played Rain in Woody Allen's Husbands and Wives (1992). In the film, Rain had an age-gap affair with Gabe Roth (Woody Allen), her Columbia College literature professor. And she had age-gap affairs with her friend’s father, her father's business partner, and with her analyst. 

Claudia (Kirsten Dunst) and Louis (Pitt) "Interview with the Vampire"

Lastly, a year after Pitt and Lewis broke up, Pitt played Louis in Interview with the Vampire (1994) In the film, Louis and Lestat (Tom Cruise) conspired to turn Claudia (Kirsten Dunst) into a vampire. While Lestat and Claudia’s relationship was platonic, Louis and Claudia's relationship was physical. So much so that in a scene, which is controversial to this day, Claudia (i.e., 11-year-old Dunst) passionately kissed Louis (i.e., ≈ 30-year-old Pitt).