Ryan
11) Jack McCoy
As an Executive Assistant District Attorney on “Law and Order”, Jack McCoy finds himself rubbing shoulders with some of the meanest, most hardened and clever criminals out there. With a reputation for pushing the envelope, McCoy is the type of boss who stops at nothing to ensure that justice is done. When he bends the rules, it is only so that the bad guys get what’s coming to them and the innocent party gets the redress it deserves. Most people would consider themselves fortunate to work for such a man!
12) Sam Malone
Portrayed by the lively Ted Danson, Sam Malone is the boss of the bar on the hit 80’s sitcom “Cheers.” Blue collar workers everywhere can relate to having or hearing about bosses like Malone, shown as a recovering alcoholic who is unable to let go of his glory days. On the show, Malone is most commonly seen running a bar filled with people who idolize him for his days as a mediocre relief pitcher for the Boston Red Sox. All things considered, he was a pretty easy and fun boss to work for.
13) Donald Trump
Real estate mogul Donald Trump was thrust into the TV boss realm with the airing of “The Apprentice” in 2004. On the business reality show, 15-18 contestants comprise an elimination-style competition to see who will win the right to run one of Trump’s companies for a full year. The prize doesn’t come easily though, as virtually every contestant is chastised and talked down to by Trump at one point or another. By the end of each episode, the impression is that Trump is an obnoxious and demanding boss that most people would hate working for.
14) Vince McMahon
Professional wrestling is often described as a male soap opera, and if that’s the case, Vince McMahon is definitely the ringleader. As the fictional (and real-life) owner of World Wrestling Entertainment, McMahon frequently writes himself into the storyline as a prototypical snobby, corporate businessman. On shows like Monday Night Raw, Vince can be seen interfering in wrestling matches, forcing title holders to defend their championship belts, or even firing people on national television. Unlike many bosses, however, Vince McMahon is not afraid to get his hands dirty and settle employee-employer disputes the old fashioned way!
15) Jack Shepard
Jack Shepard may not be the boss of an office or a space ship, but his job is still a pretty tall order. As part of a group of plane crash survivors stranded in a remote jungle, Shepard quickly finds himself thrust into a leadership role. In this way, Shepard portrays the role of the “unwilling” boss who people naturally begin deferring to in recognition of his leadership qualities. Although he does not like this at first, he eventually becomes comfortable enough to just accept it.
