How Shiloh Jolie-Pitt Once Pranked Brad Pitt

After Angelina Jolie was granted physical custody of the six children she shares with ex-husband Brad Pitt — Maddox, Pax, Zahara, Shiloh, Knox, and Vivienne — sightings of Pitt and the kids together ceased. But Pitt would continue fighting Jolie for joint custody in court for years, per Page Six, while reportedly taking advantage of his visitation rights behind closed doors. "[He] pushes to see them as often as possible wherever they all are in the world," a source told Us Weekly of his relationship with the brood. According to the insider, he also made an extra effort to make Shiloh Jolie-Pitt's 16th birthday a special experience.

There was a time when it wasn't uncommon to see Pitt out and about with his oldest biological daughter. In 2013, he was photographed chowing down on Japanese food with Shiloh and Zahara Jolie-Pitt in Madrid, and a year later, he and Jolie were spotted cheering for the two girls at a soccer game.

In a 2014 interview with Radio Times, Jolie spoke about Pitt's special bond with his daughters. "Brad thinks the girls can do no wrong. He's mush in their hands!" she revealed. He even let Shiloh get away with playing a prank on him in a rare father-daughter moment that was captured on film.

Despite her famous name, extraordinarily wealthy parents, and jet-setting lifestyle, Shiloh Jolie-Pitt developed the personality of your average fun-loving, energetic kid. "Shiloh's hysterically funny, one of the goofiest, most playful people you'll ever meet," Angelina Jolie told Vanity Fair in 2010. Fans got to see Shiloh's silly side in a featurette for the 2015 movie "By the Sea," which Jolie directed and starred in alongside Brad Pitt. The drama was filmed on a Mediterranean island off the coast of Malta, and Jolie told Vogue that she and Pitt considered the work trip their honeymoon. The couple also made the unconventional move of bringing their kids with them.

When young Shiloh joined her parents on the set of their film one day, she kept herself entertained by playing with a few mischievous toys. She was captured on video shooting a slingshot, and later pranking her pops, who was asleep at a table, with what appeared to be a toy gun. In the clip, Shiloh seemed to fire over her snoozing father, causing Pitt to jolt awake and exclaim, "Damn it!" Luckily, he had plenty of experience dealing with his children's various other projectiles by then. "I'm impervious to poo, snot, urine, vomit. You can't get me. You cannot break me down," he once declared on "Oprah."

When he appeared on "Oprah" in 2008, Brad Pitt revealed that Shiloh Jolie-Pitt went through a phase where she became so obsessed with "Peter Pan" and she would only respond to the names of two characters from the beloved children's tale, Peter and John. In Disney's animated movie based on the story, Wendy is trying to master the art of flying when some of the Lost Boys use slingshots to shoot her down, so perhaps this explains where Shiloh's fondness for one of her so-called weapons came from.

When Angelina Jolie was tasked with bringing a different Disney character to life, the "Sleeping Beauty" villain Maleficent, she learned that her adventurous daughter wanted to try her hand at mastering another weapon. In a 2014 interview with The Hot Hits, Jolie revealed that she asked Shiloh if she wanted to play a younger version of Princess Aurora in "Maleficent," but her daughter had no desire whatsoever to dress up in a gown. Instead, Shiloh offered to play a character of her own creation named Marcus. "I said, 'Who's Marcus?'" Jolie recalled. "She said, 'Marcus has horns and a bow and arrow.'" So there's your "Maleficent 3" plot, Disney.

Shiloh Jolie-Pitt has always been a bundle of energy as evidenced by the hobbies she's pursued. Surprisingly, none of them involve shooting anything — but they're still pretty dangerous. When she was 5, Shiloh became a big fan of taking four wheelers out for a spin with her dad. "She doesn't want to learn about the brakes. She just wants to go!" Angelina Jolie told Marie Claire (via the Daily Mail). And while talking to E! about how Shiloh celebrated turning 8 years old in 2014, Jolie revealed, "She's a skateboarder. We did graffiti lessons and skateboarding." The actor even had to deny her daredevil daughter's request to use the set of a Hollywood Reporter photoshoot as her own personal skatepark.

But, while Shiloh once seemed like she was potentially destined for the X Games, a viral video of the teen dancing to Lizzo's "About Damn Time" had "Step Up" star Jenna Dewan jokingly trying to recruit her for Season 2 of the reality series "Come Dance With Me," per Elle UK. In 2022, an insider told Us Weekly that Shiloh had been taking dance classes for years, and her father was seriously impressed with her skills. "I don't know where she got it from," Pitt told Entertainment Tonight. "I'm Mr. Two-Left-Feet here." He did, however, bust a move at the "Bullet Train" premiere, so he and Shiloh would likely make a formidable team on "Come Dance With Me."