The Worst Bosses In TV History…And Some of the Best

David B Morris
7 min readFeb 10, 2022

Part 1: The Worst People in TV To Work For

Never worked a day in his life..and proud of it.

Late last night while perusing the web I found one of those blogs listing ten of the worst people in television history to work for and ten of the best. Having seen quite a few of the series these characters appeared on, it was really hard to disagree with a lot of their choices. No one would willingly want to work for Louie on Taxi or Michael Scott on The Office. But I’d like to have an employer like Lou Grant or Ron Swanson. Who wouldn’t?

And because I’ve spent so much of my life watching TV, I was quick to notice that the writers of that post had left out quite a few ‘horrible bosses’ and quite a few wonderful ones. There have been plenty of examples of each during the era of Peak TV and it is often because of the mastery of their performances that we end up loving some of the best and hating the worst. (Though to be clear, there are quite a few horrible ones that I really think the writers did terrible work on.)

So, as the world gets back to work, here are some bosses we should be grateful we’ll never work for…and some we definitely wish we had. We’ll start out with the truly horrible and (in some cases) monstrous:

Horrible Ones

Roger Sterling, Mad Men

Anyone ever wants to point out the perfect example of white male privilege; you really don’t have to go much further than the man behind so much of the trouble for Don Draper. Almost certainly a legacy hire (his father founded the agency with Bert Cooper) he spent his time at three different firms doing as little work and as much partying as possible. He left his wife for his secretary in Season 2, sold the firm to the British for more money, lost the Lucky Strike account (the one big account the firm had) because he didn’t put in any effort and kept having extramarital affairs, doing LSD, and completely disregarding his family. In the hands of any other actor than John Slattery, the viewer would have had hated Roger pretty much from the pilot. But because he really seemed to be so much of a product of his time (and let’s face it, Matthew Weiner and company pretty much gave all the great one-liners on the series) we were always charmed by him. He would have been lousy to work for, but it would have been a gas doing so.

Arvin Sloane, Alias

There are some terrible employers on this list. I don’t think many of them lied that they were working for the CIA when they were actually running an evil espionage organization. And you know, killed one of their interns’ boyfriend in the Pilot. But this was just the start of the betrayals that Sloane would bring down just about everybody he ever met, every friend and everyone he ever loved in this criminally underrated spy series. What is perhaps the most remarkable thing about Sloane is how long he managed to keep surviving after everybody knew of all of his treason — less than a season after SD-6 collapsed, he’d convinced the government they could trust him and by season 4 he was working for them again. The brilliant character actor Ron Rifkin gave, in my opinion, his greatest performance as a silver tongued devil none of the other characters trusted and yet had to keep doing anyway year after year. Throughout the series he pursued one mythical goal without let up — and in the finale he finally realized it, and actually got a fate worse than death.

Richard Fish, Ally McBeal

Though his character technically was created by David E. Kelley a full decade before Mad Men was created, one finds Richard Fish (Greg Germann) a spiritual heir to Roger Sterling. He was the head of a law firm who made it perfectly clear he cared nothing for the law (I could never understood how he graduated from law school) and only for money. These days, it’s hard to imagine him surviving the #MeToo era, with his unisex bathroom and having absolutely no problem touching the necks of every woman he met. He had no interest in being monogamous (it’s a question he’d know what the word meant without looking it up), and had no problem blatantly telling female employees he’d promised a partnership too in order to hire that he had no intention of following through because then he’d get less money. Not to mention his obvious trans-phobia, but that’s something quite a few of the characters had. All Fish every cared about was having fun, sex, and making money — working not part of it. Now whether you had a problem with this at Fish and Cage is a question that is unclear (there was a fair amount of turnover, but that was true with every David E. Kelley series). The one thing you can’t argue is that working for Richard Fish was a constant headache.

Helicopter accidents only made you hate him more.

Robert ‘Rocket’ Romano, ER

It was a tossup whether Kerri Weaver or Robert Romano was going to fill this spot — both of them were prickly, had far more enemies than friends, and kept telling all the doctors at Country General what a lousy job they were doing. But in the end, it’s no contest. Forget that Romano was accused of sexual harassment, was probably racist and homophobic well before he got the job of Chief of Staff. Romano very quickly handed off all of the actual duties to his subordinates (particularly the long-suffering Elizabeth Corday) and then spent his days in surgery or telling everybody who came in sight what a horrible job they were doing. (I actually consider the drop in quality of ER as a series concurrent with Paul McCrane, who played Romano, becoming a regular.) He was such an insufferable character, that when he got his arm cut off and reattached, he actually became less likable as he fell from power. When his character ended up getting crushed by a helicopter in the middle of a crisis in Season 10, I’m not surprised that nobody noticed he wasn’t present or that anyone came to his memorial in the next episode. When Elizabeth, practically the only attendee, told us: “He had no wife, no family. Nothing but this place,” my reaction was basically: “It’s a good thing for humanity.” Weaver said: “He’ll be missed.” Trust me, he wasn’t.

Eli ‘Rowan’ Pope, Scandal

Again there are a lot of possible options for horrible bosses on this series — Cyrus Beene basically excused stealing elections by saying he deserved to be President and Olivia Pope herself was no saint to work for. But again, there’s no real contest. Rowan’s job as head of B613 was basically to have operatives who were torturers and assassins and he had no use for any of the powerful people he was essentially trying to protect. But alone among all these horrible bosses he had no respect for the institutions he was killing for. He would say B613 was there ‘to preserve the republic’ but it was clear by the end of his first full season as his regular that all he cared about was being in control of everybody — including his own daughter. He was simply a monster who showed no repentance for the horrible things he did or for the Presidents he constantly brought to heel. His last real act on Scandal was to brag before a Senate hearing about all the horrible things he ever did and practically daring him to punish him. Joe Morton is one of the great character actors of our time, but the Emmy he received for Scandal is frankly one of the least deserved ones in the shows history. We might have all been working for Command which may explain why everybody in Olivia Pope’s world was so messed up. (And I doubt there was much of a retirement plan.)

Claire Underwood, House of Cards

It is perhaps inevitable I wrap up with House of Cards which had two of the most manipulative people in the world as leads. Am I being a bit sexist in saying that Claire was a worse boss than Frank? Honestly I don’t think so. Throughout the three seasons I have watched the series (and I know more than enough spoilers for the last three to prove me out) Claire almost always proved she was as ruthless as Frank when it came to achieving her goals. In the first two episodes, she had an employee who disagreed with her fire half her staff and then made her the last employee let go. She would foil a critical piece of legislation to get something for her company. After firing a pregnant woman, she told her: “I will have your unborn child strangle itself in its womb” and she was willing to use her sexual assault by a military figure as an alibi for an abortion — then throw one of his victims under the bus to guarantee her ambitions would be realized. And all of this was before her husband became President. I always felt that Robin Wright’s work as Claire Underwood was by far the breakout performance of House of Cards and it was magnificent all the way through. That said I would never have counted on her as being a good reference — assuming, of course, you survived working for her.

Now that you’re all counting your blessing that you never worked for any of these people, in the next article I’ll deal with some people you might well give a World’s Best Boss mug to — and it wouldn’t be ironic.



David B Morris

After years of laboring for love in my blog on TV, I have decided to expand my horizons by blogging about my great love to a new and hopefully wider field.