Best of the Worst TV Bosses

It’s just about Labor Day, and employees across the country are taking a hard-earned three-day weekend to escape the daily grind of their work weeks.

While a slew of the U.S. workforce certainly fancies what they do for a living, others feel complete disdain toward the day-to-day rigors they must deal with in the name of bringing home the bacon — and this almost always has something to do with the attitudes, demands and presences of their bosses.

Tony Soprano was one kind of boss.

Ironically, it’s some of our favorite TV shows that serve as mellow-out time, allowing us to remove our attention from the mental turmoil of those 40-plus hour work weeks. Though we’re inclined to live vicariously through our dearest characters, a handful truly scare us — at the prospect of being under their supervision.

Much like the real world, scripted TV authority figures come in all kinds — narcissistic, dictator-like, scapegoating and manipulative, to name a few. In some cases, a few of the most deceptive head honchos were, and are, killers.

Jersey mobster Tony Soprano in HBO’s “The Sopranos,” for example, played by the late James Gandolfini, was based on a real-life DiMeo crime family capo. Gandolfini’s portrayal of the mob boss struck such a chord with cable TV viewers that it earned him three Emmys.

In honor of Labor Day and bosses everywhere, here are five other small-screen big kahunas who might make you actually look forward to heading back to the office on Tuesday morning.

Don Draper of ‘Mad Men’
Depicted for his “agelessness” by The New Yorker, actor Jon Hamm’s representation of post-Cold War creative director Don Draper finally nabbed him an Emmy in “Mad Men’s” farewell season (2015).

Although the 1950s advertising firm bigwig embodied many of the qualities of a true leader, there were several other traits that would make sharing a boardroom with him considerably less than ideal — i.e. women-demeaning, an inclination for tipping the old bottle back, and personal identity battles. Make no mistake about it: Hamm’s bad boy antics had a majority of America swooning. However, those same attributes would undoubtedly raise their blood pressures if they ever sought employment underneath him.

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Ari Gold of ‘Entourage’
Making it big-time in Hollywood is no easy feat, by any stretch — so when someone does climb to the top, it’s definitely an achievement to bask in. Regardless, that very novelty would quickly wear off if you worked alongside “Entourage’s” Ari Gold, played perfectly by Jeremy Piven.

Although the program centered around fictitious Tinseltown A-Lister Vinnie Chase (Adrian Grenier) and his Queens posse’s journey through the film industry’s ups and downs, it was Chase’s uncomfortably boisterous, crazy, amped-up agent that always seemed to take center stage. Sure, Gold’s uber-aggressive ways would land him boatloads of top clients — Mark Wahlberg, Eva Longoria, etc. — but his high strung personality would drive the most sane of employees to a psych ward; just ask his assistant, Lloyd (Rex Lee).

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Gregory House of “House”
Those working alongside Dr. House on Fox’s “House” were far from zen when they were forced to listen and agree with his abnormal diagnostic approaches — let alone those that entrusted him with their care. Hugh Laurie’s character was also a recreational drug user, whose leg infarction became the catalyst for a Vicodin addiction. While the actor’s portrayal of the curmudgeonly MD won him two Golden Globes, laboring alongside such an egomaniac could be a recipe for malpractice.

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Michael Scott of ‘The Office’
“The Office’s” Michael Scott was far from being Dunder Mifflin’s company man. Steve Carell’s work as the mockumentary show character followed comedic mastermind Ricky Gervais’ portrayal on the British version. Michael’s affinity for interpersonal incompetence ultimately resulted in the repeated mental demises of several workers. Regardless, Michael almost always puts on a chummy display. Nonetheless, his love of comedy continuously got him into trouble.

Being bogusly fired and sexually harassed are just two of the many mishaps that would have you impolitely declining 40-hour weeks inside the paper distribution confines with Scott.

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Frank Underwood of ‘House of Cards’
Kevin Spacey not only paved the way for Netflix original programming, but also blazed a trail for TV binge-watching. The veteran actor’s portrayal of corrupt commander-in-chief Frank Underwood in “House of Cards” continuously poses us with the most outlandish of “what if” scenarios pertaining to the US government.

While it has been done many times over, no one has broken the fourth wall quite like Underwood, who has two murders on his resume; journalist Zoe Barnes (Kate Mara) and Rep. Peter Russo (Corey Stoll). Not even the Secret Service could save you if you were caught in President Underwood’s crosshairs, whether that was inside or outside the Oval Office.

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