18. Salvatore Romano (Mad Men)
Salvatore Romano, better known as Sal, is a former employee of the Sterling Cooper ad agency. Using his keen eye, Sal helped bring an aesthetic quality of the work conducted by Don Draper and crew as the art director for the company. Unfortunately, Sal's life was more complex than simply boozing and man-whoring around while dealing with a horrible wife and unhealthy dose of self-loathing. Being a closeted gay man must always be difficult. Even more so when you're in the less tolerant 1960's and trying to juggle a sham marriage with your career. But Sal even has to contend with the unfair standards set by Sterling Cooper. Ultimately, he's fired when he refuses to give into another man's sexual advances. Sal would've deserved a full series on his own, setting out to discover his identity in an era and profession that was remarkably intolerant in its faux civility.