Saturday Night Live
By portraying the ad's "It's Not That Complicated Guy" for AT&T, it not only made him an easy $250,000, but it also helped him snag himself a role on the coveted live comedy show, Saturday Night Live. He's been playing political characters like Donald Trump Jr. and Mitch McConnell for several years starting in 2013. He also had an online web series. However, Bennett's reign of hilarity doesn't look like it's ending any time soon.