Don Draper
Jon Hamm | "Mad Men"
Don Draper plays by his own rules, a true “man’s man.” He is a successful debonair badass with the confidence of a prizefighter and the liver of a Kennedy. Draper spreads the love all around. When he isn’t sleeping with his secretaries, he promotes them –well- one. Draper is human of course, he is introspective, he cries, he screams, he carries catholic guilt around with the best of them. At the end of a long day, or the beginning of one, Draper will be the boss to sit down and pour you a drink; just don’t make a habit of going to lunch with him.
Ari Gold
Jeremy Piven | "Entourage"
Ari Gold is something of an anomaly; A Hollywood super agent who is young, quick witted, unflinching, and merciless, yet funny, amiable, loyal, and a family man. Ari is a verbal assassin with retorts quicker than a bullet train. Whether it is an assistant or colleague no one is safe. Ari is an equal opportunity lender when is comes to handing out verbal lashings. Who else can tell their assistant “I will choke you out with a strap on” and still be charming?
Walter White
Bryan Cranston | "Breaking Bad"
Walter White is the wild card of the list; A high school chemistry teacher cum cancer victim cum meth chemist extraordinaire. Boss of one, White and his protégé Jessie Pinkman outsmart drug dealers, take down Mexican drug lords, and transform the meth trade in New Mexico. A desperate man’s modern film noir hero—White means well…sort of.
Dr. Gregory House
Hugh Laurie | "House"
House is an amalgamation of sorts. The good Doctor is a medical wizard with the razor sharp wit and sarcasm of Ari Gold, the ego and impatience of Don Draper, and the couth of Larry David. Being employed by House not only means you get to solve medical mysteries, but you also get to break into people’s houses and go through their stuff.
Jack Donaghy
Alec Baldwin | "30 Rock"
Ol’ JD is the epitome of alpha male; A smooth talking mellowed out version of Gordon Gekko. Jack came from modest South Boston, attended Ivy League Schools, and rose to VP of Television at GE. Taking a note from Hemingway, Jack climbed Kilimanjaro, bow hunted Polar bears, and sparred with Chuck Norris. With elocution slicker than Obama, Jack’s retorts are so breathtakingly hilarious you would almost think they were crafted by the writers at SNL.
Dr. Cal Lightman
Tim Roth | "Lie To Me"
Cal Lightman’s covert near death FBI contracted escapades have given hope to thousands of hopeless undergraduate psychology students everywhere. The fact that he is a human lie detector who can read micro facial expressions is probably not fantastic if you work for him or are related to him or have any sort of dealings with him whatsoever-but it makes for great television.
Michael Scott
Steve Carrell | "The Office"
Michael Scott is a loser whose jokes always backfire. He is annoying, immature, offensive, and conceited. Many people, at one point or other, have had terrible jobs with terrible bosses. After work, the television goes on to dull the pain of our feckless workday. It’s odd that after a rough day at the office the first thing we want to watch is “The Office.” Secretly, we all really want Michael Scott as our boss.
George Christopher
Ted Danson | "Bored To Death"
George Christopher is the farcical bon-vivant New York magazine mogul who leaves you scratching your head as to how he became so successful. He smokes dope, drinks too much, parties to much, shows hints of insecurity, and is constantly trying to stay relevant. Christopher is the type of boss who is pretty much up for anything, a true partner in crime.
Notable Mentions:
Roger Sterling (John Slattery “Mad Men”)
Eric Northman (Alexander Skarsgard “True Blood”)
Steve Buscemi (Enoch “Nucky” Thompson “Boardwalk Empire“)
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