8. Handsome Jack (Borderlands 2)
Ever known somebody whos a complete asshole but you love them anyway? Enter my abusive relationship with Handsome Jack, the chief antagonist of Gearboxs blockbuster sequel. Jack is the president of the Hyperion corporation and the self-declared dictator of Pandora. Much of Jacks interactions with the player are done via the players communicator and often display the Hyperion honchos love of juvenile humor. Just bought a pony made of diamonds, because Im rich, so, you know, thats cool, he tells you when he contacts you for the first time. For that rest of that particular quest, he continues to call you and give you updates on what hes going to name his diamond pony, which is an actual pony made of diamonds. He christens the beast Butt Stallion. This is the guy youll be listening to all the way through your lengthy adventure on Pandora. However, hes surprisingly more than just a simple combination of dick jokes and maliciousness. As the game goes on, an unlikely, almost sympathetic depth to his character is revealed, if you take the time to look around for audio recordings related to Jacks history. I say almost sympathetic because his origin story doesnt change the fact that he murders several of your chums, so uh, yeah, screw Handsome Sadsack and his weepy story.