3. Hank Scorpio
First appearance: “You Only Move Twice” (Season 8, Episode 2)
Voiced by: Albert Brooks
If you ever wondered what would happen if Bill Gates suddenly turned into a maniacal Bond villain, look no further than Hank Scorpio. As the owner of the Globex Corporation, Scorpio is both a savvy businessman and a twisted megalomaniac armed with a laser satellite system capable of turning any major city to dust. Of course, he also happens to be Homer’s boss for an episode. Voiced by the brilliant Albert Brooks, Scorpio possesses a collection of memorable quotes, a handsome beard, and a sociopathic personality.
For some reason this supremely brilliant and wealthy mad man takes a shine to Homer, who's completely oblivious to his new boss’ murderous streak, despite having ringside seats to Scorpio’s final throwdown with the U.N. From hammocks to homicide, Scorpio is the perfect blend of sharp writing and pitch-perfect voice acting by Brooks, who manages to make a mass murderer sound like the world's best boss.