Since 1994, Leo and Tobey have counted A Tribe Called Quest frontman Q-Tip as a friend. In an LA Times interview in 2008, the rapper said of Leo, "That's one of my best friends and I'm one of his. That's just my boy. Tobey's my boy. We all love sports. We're all into politics. We all have a stake in the artistic community. We all have a lot of similar interests."