Gavin Belson (Silicon Valley)
It take some serious skills and an extra amount of effort to pull off a winning within the context of a comedy series, particularly in a multi-faceted way that doesn’t just show them being an a-hole to everyone, and that’s what makes Matt Ross’ Gavin Belson stand out. As the not-exactly-genius head of Hooli, Belson has “success” as his motivation, and if someone else can’t or won’t help him get there, that’s when he becomes a force to be reckoned with. But he’s also never shown as being completely infallible, even as the leader of one of the biggest companies in the world, and watching him take on Richard and Pied Piper was never boring, as you could never tell when Mike Judge and his creative team would actually let Pied Piper win.