The SNL Hero
By playing the "It's Not That Complicated Guy" for AT&T, it not only made him a cool $250,000, but it also helped him snag himself a role on SNL. He's been playing characters like Donald Trump Jr. and Mitch McConnell as if he was one of their distant family members since 2013. Bennett's reign of hilarity doesn't seem like it's going to end any time soon.