Three-year-old Maddox’s spiky locks were a bluer hue at the 2004 Venice Film Festival—what better place than Italy to push the follicle envelope? 2004 turned out to be a busy year for Maddox and his mom—Angelina filmed Taking Lives, Sky Captain and the World of Tomorrow and Alexander, and provided the voice of Lola in Sharktale. Of course, she slowed down the following year and only made one movie, Mr. and Mrs. Smith...

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