2. Domingo (Kid Cudi); How to Make It in America

As a weed-dealing dog-walker in his mid 20's, Domingo leads the ultimate slacker lifestyle. He doesn't do anything remotely worthwhile with his days and yet makes obscene amounts of money, all while hanging with friends and romancing various bad women, most notably hottie pot customer Rachel (Lake Bell). In between his dual enterprises, dude manages to rock one wildly different, yet successful outfit per scene. And he's not even involved in the show's central fashion line.

Despite the recent, unfortunate canceling of How to Make It, as it stands in the HBO legacy, Dom has managed to emerge as one of HBO's most stylish characters in only sixteen episodes. Is he fly because he has nothing better to spend his money on, or does the fact that he's played by one of the most stylish rappers out have something to do with it?