The 12-year-old was there to watch a very proud moment for his mum, who was awarded an honourary Oscar; the prestigious Jean Hersholt Award for humanitarian work.
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Maddox smiled as he posed with his parents outside the Academy of Motion Pictures Arts and Science's Governors Awards on Saturday night. His smart look was a world away from his usual casual style of jeans and trainers.
Brad – who was dressed identically in a tuxedo and patent shoes – put a protective hand on his son's shoulder as they walked inside the Grand Ballroom at the Hollywood and Highland Center where the ceremony took place.
Maddox has lived most of his life in the spotlight travelling the world with his A-List parents. His life changed dramatically the moment Angelina took him to live with her in the US in 2003 after visiting his Cambodia homeland.
She adopted him in 2002 when he was seven months old, but legal issues had delayed her taking him from his orphanage in Phnom Penh.
The brunette star had first applied for adoption in 2001 when she visited Cambodia while filming Lara Croft: Tomb Raider in 2001, returning on a field mission for the United Nations' High Commission for Refugees.
She had planned to raise the little boy with her ex husband Billy Bob Thornton, but after they split became a single mum. Then Brad came into their lives, and it was actually the little boy who was the deciding factor in them taking their relationship to the next level.
Maddox encouraged them to get together, when "just out of the blue called (Brad) Dad," says Angelina.
"It was amazing. We were playing with cars on the floor of a hotel room, and we both heard it and didn't say anything and just looked at each other. So that was probably the most defining moment, when he decided that we would all be a family."