1 of 14
Nine-year-old Maddox helps mom Angelina Jolie rein in his siblings Zahara, 5, and Pax, 6, while the brood – including Shiloh, 4 – makes their way through Japan's Narita International Airport on July 26. The Salt star recently dished on her kids' close bond, telling Parade: "The children talk to each other, and they look out for each other, and they have each other."
2 of 14
Who's old enough to hang ten? While Mom and Dad keep a close eye, Maddox rides the waves at a Malibu beach party during Memorial Day weekend.
3 of 14
4 of 14
While the rest of the brood is home with the babysitter, Jolie and Pitt treat Maddox, 8, to a big night out for the Invictus premiere in Beverly Hills on Dec. 3.
5 of 14
Then 7, Maddox – and little bro Pax, 4½ – is old enough to join his parents on a tour of a Ninth Ward housing project in New Orleans in Oct. 2008. "I usually explain to them that there are other families in the world that aren't as fortunate as ours," Jolie shared with CNN on teaching her children the importance of giving back.
6 of 14
While pregnant with twins Knox and Vivienne, Jolie keeps Maddox close during a family boat trip with dad Brad and brother Pax in Monaco in May 2008. By then, the 6-year-old had traveled the world over right by Mom's side, even returning to his home country of Cambodia in 2006. "He recognized himself in the people," Jolie said of her son, "which is a wonderful thing."
7 of 14
Though Jolie says Maddox is now at an age where "the boys are kind of hanging out," he and little sister Shiloh, then 16 months, show they can also play nice during a visit to New York City's Kidville in Sept. 2007.
8 of 14
Knox and Vivienne aren't the only twins in the family! Stars-in-the-making Maddox, 6, and Pax, 3½, hang out with mom for fun day in New York's Central Park in Aug. 2007. "It became clear to us that it might be important to have somebody around who is similar to the other children so they have a connection," Jolie told Reader's Digest of her and Pitt's decision to adopt a son from Vietnam. "Mad's very excited that his brother is from Asia."
9 of 14
Hold on! Maddox catches a ride on Dad's back on their way to a rare boys' only outing in New York City in June 2007. And while sharing Mom and Dad's attention with five younger siblings can't be easy, the youngster seems to relish the role of big brother. Upon the arrival of his twins in '08, Pitt told PEOPLE of his eldest child, "This is Mad's fourth/fifth time becoming an older bro. He's asking when we can have more."
10 of 14
TOUR DE FRANCE
While waiting to ride the carousel at the Eiffel Tower, Maddox, 4½, is literally a Paris match with mom during a visit to the City of Light in Feb. 2006. Three years earlier, the tattooed star got outfitted with a permanent reminder of her little guy – a Buddhist prayer of protection tattooed onto her left shoulder blade, for which she traveled to Thailand to get.
11 of 14
MAKING THE GRADE
Maddox is "very smart but he's got a certain sense of calm," Jolie told PEOPLE in 2006. Here, the actress walks her little "intellectual," whom she says is "great at school, great at history," to school in Malibu, Calif., in Dec. 2005.
12 of 14
A SMALL REQUEST
Just three months after adopting Zahara, Jolie strolls a Malibu beach with her two leading men – Pitt and Maddox – in Oct. 2005. "My son is in love with Africa, so he has been asking for an African brother or sister,"a the actress said of her then-4-year-old, who first visited the continent when Jolie filmed 2003's Beyond Borders.
13 of 14
Look ma, no hands! Jolie looks on with a mother's pride as Maddox, 3½, take a spin on the carousel in New York City's Central Park in June 2005. Affectionately nicknamed "Madness," Jolie proudly noted in 2002 that her Mohawked cutie's "hair stands straight up, like he was born a punk rocker."
14 of 14
Jolie credits Maddox, whom she adopted at 7½ months from a Cambodian orphanage in 2002, with saving her life. "For me, becoming a parent changed everything," she told PEOPLE in 2003. "My priorities straightened out. My life is all different."