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). 

THE CUT and WALL STREET JOURNAL: How Young Is Too Young for a Crop Top?

Whitney Friedlander shared in The Cut piece “The Dread of Your Kid Asking to Wear a Crop Top” (N.D. 2025) that her 5-year-old daughter is “obsessed with crop tops”! Consequently, Friedlander is “queasy”, because, in her opinion, crop tops represent vulnerability. Friedlander:

For the past six months, ever since she saw a friend wear one at school, my daughter has been obsessed with crop tops. She’s 5.

The whole idea of my young daughter wearing a midriff-baring tee makes me queasy. It’s not the shirt itself but what it represents. ​​I cannot explain to her why simply wearing some trendy item of clothing makes her vulnerable in ways I never want her to understand 

Friedlander reiterated that her daughter desires to wear crop tops only because her daughter’s friends wear crop tops.  Friedlander:

And the reason she wants them is simple and glaringly unoriginal: Her friends get to do it.

Friedlander asked Lyndon and Carla, her “daughter’s crop-top-wearing friends’ parents”, about their daughter’s crop top, but they claimed that they had no idea how their daughter got a crop top. Really? Friedlander:

I asked my daughter’s crop-top-wearing friends’ parents, Lyndon and Carla, if they recall the impetus for what was clearly a life-changing moment for at least one person. Nope. In fact, they don’t even know how she ended up wearing it [...]

[...] In any case, they said they’d never knowingly put their kids in a crop top and wouldn’t have bought one — not that they’re judging parents who do.

In addition, Friedlander wrote that her daughter became attracted to crop tops because crop tops are a part of the zeitgeist, which hit a “fever pitch” at day camp, where her daughter observed “real teenagers [in crop tops] out in the wild”. [GIF deli]

Even asking my daughter how she learned the term “crop top” came with a blank stare. They’re simply an ingrained part of her world [...] They also hit a fever pitch this summer when she went to a day camp held at the neighborhood high school and saw real teenagers out in the wild.

Casey Lewis, the After School Substacker, shared with Friedlander that, in addition to crop tops, tube tops, and spaghetti-strap tops worn with midriff baring super-low rise jeans are popular with teens. Friedlander:

Casey Lewis, who runs the popular After School Substack, has watched a lot of back-to-school hauls the past few months from middle-school- to college-aged kids, which is the sweet spot for my daughter’s adulation. Lewis says “it’s all about tube tops and girls are wearing these super-low jeans and they’re showing their bellies and spaghetti-strap tops.”

Friedlander wrote that another reason her daughter wants to wear crop tops is that wearing crop tops gives her 5-year-old daughter the confidence to “hang with the cool teenager who was the assistant in her ballet class.”

Even though my daughter doesn’t own a phone or have her own app log-ins for mine, the abundance of content on TikTok or Snapchat inevitably trickles down. Somehow she instinctively knows what kind of wardrobe choices will make her feel like she can hang with the cool teenager who was the assistant in her ballet class.

Friedlander related that at a sleepover, matching crop tops were distributed by a parent to schoolgirls, and that “a kid [was seen] wearing one that said “Little Devil.” Friedlander:

One of the Reddit posters I reached out to said her daughter was given one at a sleepover by a friend’s mom who’d bought all the kids matching tops.

In my defense, the crop tops don’t always make it easy for us to take their side. My friend Cybil [...] has no qualms with most crop tops but even admitted to giving the side-eye to a kid wearing one that said “Little Devil.”

Unlike Lyndon and Carla, Friedlander openly condones (pre) tween crop tops; however, Friedlander bought her daughter some camisoles to be worn under her crop tops, which will be promptly restyled by her daughter on the school bus and/or at sleepovers. Friedlander:

In either case, I bought my daughter some camisoles to wear under her shirts. Let’s see if she keeps them on at school.

[However] [s]he’s already figured out the time-honored tradition of restyling her outfit once she jumps on the school bus or goes to a friend’s house.

Dear Hannah Prep

Back in 2023, Rory Satran asked on The Wall Street Journal “How Young Is Too Young for a Crop Top?” (Oct. 27, 2023) Before attempting to answer the question, Satran wrote that Dear Hannah Prep, a Dallas-based boutique, stocks “[...] crop tops. Lots and lots of crop tops” for “mini Swifties and Alabama sorority girls-to-be”. Satran wrote:

For mini Swifties and Alabama sorority girls-to-be, the Dallas boutique Dear Hannah Prep [...] is chock-full of everything a tween girl might want to wear for home games, slumber parties, screenings of the “Barbie” movie, or a school dance. Arranged in rainbow-colored stacks are: [...] crop tops. Lots and lots of crop tops. 

In a very interesting paragraph, Satran related that for “many” tweens crop tops don’t represent vulnerability, because they’re cute, innocent, and are worn to express body positivity; however, “others” find them “inappropriate”; therefore, in a bit of vindictiveness, stores like Dear Hannah Prep stock lots of crop tops despite or due to their divisiveness. Satran:

For many tweens—and their parents—crop tops are a cute, innocent way to express their burgeoning interest in fashion, and their body positivity. For others, they are inappropriate. [...] Despite, or perhaps because of, their divisiveness, crop tops for tweens have become big business.

Satran shared that Dear Hannah Prep has over 300,000 followers on TikTok and that in “almost every video, the tweens are wearing crop tops, some showing more midriff than others.” #marketing

Satran wrote that tween crop tops are “omnipresent” and are sold in “almost any store that carries kidswear these days”. For example, “from Walmart to Saks Fifth Avenue”, Zara, Shein, and “from Fendi to Stella McCartney to Versace”. Satran:

Walk into almost any store that carries kidswear these days, from Walmart to Saks Fifth Avenue, and you’ll see at least one crop top. [...] Zara has made them a mainstay of its children’s collections. On Chinese fast-fashion site Shein there are over 1,000 tween-size crop top styles [..] high-end designers from Fendi to Stella McCartney to Versace offer crop tops for tweens.

Crop tops are so omnipresent, it can be hard to find a non-cropped top for tweens and teens these days.

Satran attributed the recent rise of tweens in crop tops and their demand for more and more crop tops to tweens emulating beloved pop stars like Olivia Rodrigo, Emma Chamberlain, and Taylor Swift. Satran:

While crop tops emerged for teens and women in the groovy 1970s [...] they’ve only trickled down to the tween market in a big way in the past few years. [...] Tween-beloved stars like Olivia Rodrigo and Emma Chamberlain appear to live in crop tops. Taylor Swift wore one to the Grammys this year. It is no wonder tweens want in. Stores are scrambling to keep up with the demand.

Kelly Dowdy, of the high-end kids’ boutique English Rabbit in Beverly Hills, shared with Satran that some of her high-end prep school-attending customers only purchase crop tops. Dowdy shared,

“We have [high-end] customers who won’t buy anything if it’s not a crop top. They wear [private school] uniforms at school, and when they’re not at school they’re in a crop top.” 

And Sylvana Ward Durrett, of the “chic” website Maisonette, shared with Satran that crop tops “do well” on Maisonette. So much so that searches for the controversial attire doubled in a year. 

Interestingly, one can correctly infer from Friedlander and Satran’s reporting that crop tops are de rigueur for teens. For example, I previously wrote about the Blumarine by Marc Jacobs collab, which featured best-selling signature pieces like ultra-mini skirts, baby tees, and cropped sweatshirts. [Emphasis added] Consequently, one can expect that crop tops will eventually become de rigueur for tweens too. 

Lastly, in terms of the question: How young is too young for a crop top? Durrett opined: “[...]  I would say it’s somewhere between seven and eight.”

 

The Art of Mike Cockrill: Fine Art or (Pre) Teen Erotica? | An Introduction

Final Girl Digital posted the following Note on the Cricket Guest Substack: 

“These paintings by mike cockrill speak to me” 

The paintings that spoke to Final Girl Digital were Cockrill’s:

• “Grave Condition” (1997) 
• “Indepence Day” (1997) 
• “The Mirror Game” (1997) 
• "Clown Piñata" (2015-220) 
• “The Red Guard” (1997)
• "Interrogation"

Each painting depicts sadistic schoolgirls killing and/or torturing clowns. Of the series of paintings, Felicia Feaster, wrote in the New Art Examiner (July-August 1997) that the subjects of the paintings were circus clowns and “pre-adolescent girls in party dresses” and that the paintings were “vapid’ but that they “achieve[d] a shockingly layered profusion of meaning”. Feaster:

With their apparently vapid subject matter of circus clowns and little girls, the Baby Doll Clown Killers achieve a shockingly layered profusion of meaning. Two standards of cuteness face off as if in some apocalyptic jihad, as pre-adolescent girls in party dresses aim pistols and bayonets at the bowed heads of circus clowns who suggest an inferior race tamed by their evolutionary superiors.

"Clown Piñata"

Interestingly, "Clown Piñata" alludes to Cockrill’s other motifs slash themes, which involve sadistic and salacious schoolgirls. For example, in "Clown Piñata", the nymphet, in the already cleavage-baring yellow dress, has her white bra exposed, and the teen in the background is enjoying a smoke in her (satin) bra and panties while observing the pre-teen sadism.  

“Target”

In “Target” (2009), another painting in the Baby Doll Clown Killers series, a pre-adolescent girl has her knee in the crotch (area) of a clown, but as she paints the clown’s nose to match her crop top, another nymphet looks upon art patrons mischievously, while the strap of her tank top reveals her braless cleavage. And note that she does not have flush fountains. 

In 2006, Cockrill’s Over the Garden Wall exhibition was held at the 31 Grand in Brooklyn. Ben La Rocco posted a review of the exhibition, “100 words on Mike Cockrill”, on The Brooklyn Rail (April 2006). In the post, La Rocco wrote that Cockrill’s “garden is a place where childhood play meets adult sexuality”. Specifically, La Rocco referenced Balthus, Cockrill’s “unprepossessing” “Girl before a Mirror”, and Cockrill’s “Naughty”, which La Rocco referred to as a “tour de force”. La Rocco opined:

Mike Cockrill’s current exhibition of paintings at 31 Grand is entitled Over the Garden Wall. One part John Currin, two parts Balthus, Cockrill’s garden is a place where childhood play meets adult sexuality in an elixir equally suggestive and nostalgic. Children poised on the verge of adolescence feign poses to determine if they fit in [...] His symbolism is perhaps best when it’s subtle: his unprepossessing “Girl before a Mirror” is as effective as his art history laden tour de force, “Naughty.”

“Naughty”

In terms of Cockrill’s “Naughty” (2005), a naughty nymphet looks mischievously at gawkers while licking icing from her fingers. Cockrill drew attention to her spread legs via her brother’s hand, which barely obscures his sister’s panties. 

Figure: 1

Eagle-eyed art connoisseurs may have noticed another “Naughty” nymphet in the painting (See Figure: 1) who is walking towards the mischievous one with her white dress is inexplicably raised revealingly. 

In terms of La Rocco’s reference to Cockrill’s work being “two parts Balthus”, La Rocco was referencing the fact that Cockrill and Balthus shared the same muse, which is the suggestive nymphet. For example, if one compares Cockrill’s “Class Princess” (2003-04) and “Bunnyheart” (2003) to Balthus’ “Thérèse dreaming” (1938), La Rocco’s reference should be apparent. 

The description of “Thérèse dreaming”, which is on view at The Metropolitan Museum of Art (The Met), that is posted on The Met’s website will suffice as a description of “Class Princess” and “Bunnyheart” as well. The Met related that Thérèse is a “lost in thought” 12 or 13-year-old unmolded raw spirit whose “adolescent sexuality” is “potent” with a “lack of inhibition”; however, The Met admitted that “Thérèse dreaming” is “unsettling”.

Balthus’s model, Thérèse Blanchard, appears—as the title of this work suggests—unaware of her surroundings and lost in thought. Blanchard was about twelve or thirteen when the artist painted this canvas. [...] Balthus, like countless modern artists, believed the subject of the child to be a source of raw spirit, not yet molded by societal expectations. Many early twentieth‑century avant‑garde artists [...] viewed adolescent sexuality as a potent site of psychological vulnerability as well as lack of inhibition [...] While it may be unsettling to our eyes today, Thérèse Dreaming draws on this history.

In addition to painting salacious schoolgirls cavorting with cowering clowns, Cockrill painted schoolgirls cavorting with schoolgirls. In “Firstlove” (2008), the pre-adolescent girls, who may not even be of school age, lips lightly touch as Cockrill lowered the blonde’s dress to reveal her budding breasts, while he raised her summer dress to expose her budding bottom-grass. In “Forbidden” (2006), the touching nymphets are bottomless while the one on the left looks cunningly at gawkers while her forbidden fruit is barely covered by the leaf. And in “Adoration”, a chorus of children sing as two midriff-bared schoolgirls embrace and prepare to kiss. 

“Teasing the Blind”

In media, sapphic diversions are often depicted with age-gap affairs (e.g., Lolita\Miller’s Girl (2024)). Thus, it shouldn’t be surprising that, in addition to painting salacious schoolgirls, Cockrill depicted them in age-gap situations as well. For example, in “Teasing the Blind” (2004), Cockrill drew two schoolgirls teasing the blind as the blonde in pink smiles shyly as the girl in yellow confidently raises her dress to tantalize the blind man with what is under her white panties. 

Per the website Mike Cockrill, Cockrill, whom was “[c]lassically trained at the Pennsylvania Academy of the Fine Arts”, began exhibiting his works “in Brooklyn and the East Village in the early 1980s. In addition to his 2006 Over the Garden Wall exhibition at the Grand in Brooklyn, Cockrill’s work has been exhibited over 50 times. For example, in 1994, Cockrill’s paintings were co-exhibited in the Discontents and Debutantes exhibition at the University Galleries of Illinois State University. The gallery’s description of the exhibition relates that the paintings occupy a “precarious social interzone between fantasy and taboo [...] childhood and adulthood” and that Cockrill’s “paintings of girls on [the] cusp of adolescence exude an ambiguous eroticism”.

Discontents and Debutantes features paintings by two artists whose imagery occupies a precarious social interzone between fantasy and taboo, private and public, childhood and adulthood, and personal and media-induced realities. New York artist Mike Cockrill [...] has exhibited paintings dealing with sex, politics and dysfunctional family life since the early 80s. His monumental paintings of girls on [the] cusp of adolescence exude an ambiguous eroticism that leads us to rethink our views on voyeurism and decorum [...]

"Discontents and Debutantes" at the University Galleries of Illinois State University

Cockrill’s paintings exhibited in Discontents and Debutantes are mostly of lounging, perfectly nude or topless, girls on the cusp of adolescence, but Cockrill made their eroticism unambiguous as their legs are often spread suggestively. 

Of course, Cockrill and Balthus aren’t the only artists who utilized the allure of nymphets to sell art. Previously, to name a few, we wrote about the Disturbing Innocence exhibited at The FLAG Art Foundation in Chelsea, Petra Collins' Discharge exhibit at the Capricious in Chinatown, and Ernst Ludwig Kirchner's Marzella (1910).

Lastly, recall that Feaster opined in the New Art Examiner that Cockrill’s work is “vapid”, but in an interview with Poets and Artists (Aug 19 N.D.), Cockrill shared that his works have “a cheerfulness mixed with the darkness” accompanied by “sexually charge[d] undertones”. Cockrill: 

“There is a cheerfulness mixed with the darkness, so to speak. Little girls in party dresses conducting genocide against circus clowns.  Children’s book illustration style works with sexually charge[d] undertones.”