Angelina Jolie's son Maddox then-and-now — see his drastic transformation as he turns 23

It's certainly a special day for Angelina Jolie , whose oldest son Maddox is turning 23. It's safe to say that in many ways, the now 23-year-old changed his mother's life when they met in Cambodia.

© Rex

Angelina revealed that she "cried and cried" when she saw Maddox for the first time, because she knew he was meant to be her son. They met at the orphanage where he spent the first seven months of his life, and Angelina began the process for adoption.

Adopting Maddox was a major change for the actress, who had experienced a number of mental health and addiction issues as a teenager and young adult. It was through becoming a mother that she found stability: "I knew once I committed to Maddox, I would never be self-destructive again," she said.

© Pascal Le Segretain

But Maddox has changed massively over the years, growing from a little boy into an impressive adult within his own right.

© Pascal Le Segretain

Photos of a younger Maddox, then three years old, show that early on in his life he had bags of personality. His mom brought him along to the world premiere of Shark Tale at the 61st Venice Film Festival, where he looked totally animated as he interacted with her.

© Samir Hussein

With his black hair in tall gelled spikes on his head, he kept putting his hands on his mom's face as she looked after him at the special occasion. Meanwhile, Angelina couldn't take her eyes off her son. It seems that Maddox even charmed actor Robert De Niro, although he in turn didn't seem impressed by the great actor.

Maddox continues to join his mom at her film premieres and other special occasions, as he was photographed along with his five other siblings at the UK premiere for Eternals . Aged 20 at the time, he sported a closely cropped buzz cut and frames, as well as a grey suit for the formal look.

© STEFANI REYNOLDS

Similarly, the 23-year-old looked formal as he joined his mom at the White House state dinner for South Korean President Yoon Suk-yeol and first lady Kim Keon-hee in 2023. In the two year period since he was photographed at the Eternals premiere, Maddox had grown his hair so long that it touched the back of his neck, still sporting the glasses in his smart black suit.

In 2019, Maddox moved to South Korea where he attended Yonsei University. Angelina said of his decision: "We are all so happy, as a family, that we will have the opportunity to get to know South Korea even better through Maddox, and with him, during his studies."