Ryan
21) Walter Skinner
Every boss is eventually tested on his ability to deal with stubborn employees, and Walter Skinner of X-Files proved he was up to the challenge time and time again. Skinner walks the ultimate employee-employer tightrope, simultaneously trying to dissuade Fox Mulder from following his curiosity too far while also keeping him satisfied and covering up his occasional screw-ups to the higher ups at the FBI. While Skinner is big on integrity and following the rules, he is not afraid to challenge his superiors and will always go the extra mile for his top employees.
22) Tyra Banks
Although not nearly as abrasive as “American Idol” counterpart Simon Cowell, “America’s Next Top Model” host Tyra Banks is no easy customer. Unlike Simon, Tyra has already made a name for herself as a model, TV and film star, and carries very high expectations onto the show. Contestants have been known to wilter under the Banks’ scrutiny, and in the end, only the most beautiful (and thick-skinned) models make it to the top!
23) Bob Kelso
As the haughty chief of medicine at Sacred Heart hospital, “Scrubs” star Bob Kelso is the prototypical boss who builds himself up by tearing others down. With his eagerness to demean, insult, harass, or otherwise interfere with the lives of his co-workers and colleagues, Kelso is a monument to the backbiting and backstabbing that make people literally hate going to work every day. Even though Kelso often means well, there aren’t too many people who enjoy working for guys like him!
24) Wilhelmina Slater
Wilhelmina Slater is the type of boss who reached her status by making life miserable for all those who stood in her path. As the Creative Director of MODE Magazine on “Ugly Better”, Slater goes to outrageous extremes in her quest to become editor in chief. Her stunts include trying to sabotage the current editor in chief, manipulating the magazine’s injured, hospitalized owner, and even physically seducing the chairman of the publication. If you’ve ever worked for someone who thinks nothing of playing dirty to get their way, you already know Wilhelmina Slater.
25) Charlie Townsend
As the mysterious male boss behind the Charles Townsend Agency, “Charlie” directs the actions of three scintillatingly beautiful women who do his bidding as private investigators. While Charlie is never revealed to viewers, he is portrayed through phone calls as a very caring, protective, and even father-esque boss to each of the three women. If you’ve ever wished your boss would send you on dangerous missions to eavesdrop on secret conversations or operate a spy camera, Charlie Townsend is your man.
