One of Angelina Jolie’s children has already flown the coop signaling the early stages of the inevitable empty nest syndrome all parents feel..

On Monday the Oscar-winning beauty revealed to The New York Times that one of her three sons is on his own in New York City.

He is residing in her old apartment that she bought when she was in her twenties and just starting out in movies like Gia about doomed supermodel Gia Carangi.

Though 49-year-old The Eternals actress would not name which son it was – she has Maddox, Pax and Knox with ex-husband Brad Pitt – it is likely 23-year-old Maddox.

Pax has been seen in Los Angeles on his ebike with regularity and Knox is too young to got off on his own.

Angelina lives mainly in the Los Feliz section of Los Angeles in a $28M, 11K square foot mansion that used to be owned by film pioneer Cecil B. DeMille.

Meanwhile, Pitt lives in Los Angeles with his jewelry designer girlfriend Ines de Ramon. 

(L-R) Maddox, Vivienne, Zahara, Shiloh and Knox arrive for the world premiere of Eternals at the Dolby theatre in Los Angeles in 2021

 Jolie at the 40th Annual Santa Barbara International Film Festival: Maltin Modern Master Award Honoring Angelina Jolie at The Arlington Theatre on February 5 in Santa Barbara

Jolie shared that her son sounds like a typical dude in his 20s. ‘The other day I said I was going to pop by, and he was like can you just give me a day to clean?’ she said.

‘I thought, I appreciate that, you should clean up for your mother,’ she said, before adding, ‘But also, how bad is it?’

Maddox has his own career already. He is an assistant director, known for his work on First They Killed My Father (2017), By the Sea (2015) and Maria (2024). He was also seen on the set with mom when she filmed Couture in Paris.

Pax is 21-years-old and is living in Los Angeles. He is a budding photographer who has worked on several of Jolie’s movies including Maria.

And Knox is 16-years-old and still studying in Los Angeles.

The other children are Shiloh, Zahara and Vivienne. 

Angelina and Brad tied the knot in August 2014 during a secret ceremony in the south of France, and welcomed three children together during their romance – Shiloh in 2006, and twins Vivienne and Knox, in 2008.

They also adopted two more kids – Zahara and Pax – and Brad also legally adopted son Maddox,  who became part of Angelina’s brood before they got together.

But in 2016, it came to an explosive end after the pair got into an alleged physical altercation while on a private flight with their six kids.

Despite all six kids growing up as Hollywood royalty, the Jolie-Pitt brood are all very unique.

Shiloh’s parents Brad and Angelina married in August 2014 after 10 years together, but Angelina filed for divorce in September 2016 (seen here in 2012)

In a 2010 interview with Vanity Fair, Angelina said, ‘Mad’s a real intellectual, which I can take no credit for genetically. He’s great at school, great at history. He feels like he could be a writer or travel the world and learn about places and things.

‘Zahara’s got an extraordinary voice and is just so elegant and well spoken. Shiloh’s hysterically funny, one of the goofiest, most playful people you’ll ever meet.

‘Knox and Viv are classic boy and girl. She’s really female. And he’s really a little dude,’ the actress added.

She continued: ‘Shiloh dresses like a little dude. She likes to dress like a boy. She wants to be a boy. So we had to cut her hair. She likes to wear boys’ everything. She thinks she’s one of the brothers.’

Angelina revealed during an interview with Good Morning America that her kids don’t want to be movie stars like their parents.

Angelina stated: ‘None of my children want to be in front of the camera [at] this time.’ 

While Shiloh has spent the majority of her childhood out of the spotlight, she made her acting debut at age two in The Curious Case of Benjamin Button, alongside her dad, and had a few lines in her mother’s animated film, Kung Fu Panda 3, in 2016.

At age eight, she turned down the opportunity to be in her mom’s 2014 film Maleficent. 

Jolie with daughter Zahara at the 36th Annual Palm Springs International Film Festival Film Awards in January

‘I asked Shiloh about being Aurora, and she laughed in my face,’ Jolie told Elle at the time. ‘She said she’d be a horned creature.’ 

Her younger sister, Vivienne, ultimately took on the role and Shiloh has reportedly spent the past few years focusing on a career in dance.

In 2022, a source told HollywoodLife that ‘Angelina has made a huge effort to nurture her kids’ interests in all kinds of things’ and ‘enrolled them in everything from art classes to computer programming to martial arts and, at one point or another, all the kids have tried out dance lessons.’ 

After seeing that Shiloh was a natural at dance, the performer made a ‘big point to nurture that.’ 

‘Shiloh started out with private lessons before she joined a small studio near their house and then all through the pandemic, she was doing zoom classes. She’s very committed to it,’ the insider revealed. ‘Angelina’s amazed by how talented Shiloh is, but more than that she loves to see how happy Shiloh is when she’s dancing.’

Although Angelina – who worked with the the UN Refugee Agency for more than two decades – has not commented specifically on Shiloh’s dance, she has spoken out about fostering the unique talents of all of her children. 

‘Children should be allowed to express themselves in whatever way they wish without anybody judging them because it is an important part of their growth,’ she once said in an interview with Reuters.