The eldest child of the Jolie-Pitt clan was first adopted by mom Angelina Jolie from an orphanage in Battambang, Cambodia, in March 2002, when he was just six months old. He was subsequently adopted by dad Brad Pitt in early 2006 after the couple went public with their relationship, and eventually became a big brother to five younger siblings: Pax, 15, Zahara, 14, Shiloh, 13, and twins Knox and Vivienne, 11.
These days, Maddox is preparing to leave the nest and head off to college. Angelina told People in April that she was "nothing but proud" of her eldest son, though the family is keeping mum about what university he'll be attending. “I look forward to all he will do," she added.
In celebration of Maddox's 18th birthday, on Aug. 5, here's a look back at his red carpet moments throughout the years!
Maddox was just three years old when he posed with his mom alongside Will Smith, Robert De Niro and Michael Imperioli at the 2004 Venice Film Festival for the premiere of their animated film, Shark Tale. Quite a debut!
Five years later, Maddox had been adopted by dad Brad and was already a big brother to five younger siblings, but as the eldest, he got to fly solo and accompany his parents to the Beverly Hills premiere of Invictus, dressing up with a smart scarf and gold fedora for the special occasion.
He was fashion-forward and channeling his dad's style in a knit beanie on another red carpet a few years later, accompanying his mom, dad and brother, Pax, to the 2013 London premiere of Brad's film, World War Z.
Maddox really stepped out in style for his first black-tie event during 2013 awards season, posing with his parents on the red carpet at the Academy of Motion Picture Arts and Sciences' Governors Awards in Hollywood.
The next year, he posed solo on the carpet for the first time, rocking a stylish gray vest and slacks with a dark tie and blue shirt at the Hollywood premiere of Angelina's film, Maleficent, at the El Capitan Theatre in Hollywood.
Later that year, it was a family affair at the premiere of Unbroken, which Angelina directed. Maddox posed on the carpet with Brad and siblings Pax and Shiloh, as well as his paternal grandparents, William and Jane Pitt.
The Jolie-Pitt kids were joined by author Loung Ung and actors Kim Hak Mun and Sareum Srey Moch for a family photo at the premiere of First They Killed My Father at the Toronto International Film Festival in September 2017. Maddox served as an executive producer on the film, an adaptation of Ung's memoir of the same name, which tells the story of child soldiers and labor camps under the Communist Khmer Rouge regime in Cambodia.
Maddox and Pax also suited up for the New York City premiere of First They Killed My Father later that month, posing for pics with Angelina, who directed the film.
The eldest Jolie-Pitt siblings (minus twins Knox and Vivienne) posed with their mom and and artist Prune Nourry at the opening night of Nourry's documentary, Serendipity, at the Museum of Modern Art in New York City on Feb. 21, 2019. Maddox was dapper in a black suit jacket, white shirt and jeans and looked all grown up rocking a mustache!
A few nights later, the siblings were all together again as they attended a special screening of The Boy Who Harnessed the Wind at the Crosby Street Hotel in New York City.
Happy birthday, Maddox! See more about the eldest Jolie-Pitt kid in the video below.