"I wanna be free. I wanna just live. Inside my Cadillac. That is my shit." Macklemore's obsession and appreciation for the iconic image of a Caddy on white walls is obvious. He raps about it, like the line above from "White Walls" on The Heist, he photographs it, and oh yeah, he drives one, too. His Instagram is full of old-school whips that your grandad had, and he doesn't quit there. He's got bikes, skateboards, and planes to match. Check out Macklemore's 35 Best Rides Photos on Instagram.