We know it’s an old show, but it’s always fun going back and analyzing some of the old dynamics that helped make the show great, especially when we can relate it to the world of office space, our professional lives, and our bosses!

In the absurd world of Seinfeld, one thing is clear: none of the main characters are safe from their boss’s eccentricities.

From performing bizarre tasks to slipping their boss a mickey for payback, each workplace environment in the world of Seinfeld brings their unique flavor of chaos. But who among these titans of insanity would you actually want to work for? Let’s break down seven memorable Seinfeld bosses, weigh the pros and cons, and crown the ultimate workplace overlord.
 
1. J. Peterman (The Fashion and Travel Guru)

Pros: Easily fooled. Well-spoken. Possible relocation of the company to Myanmar at any moment.
Cons: Endless lectures of irrelevant personal adventures, ridiculous degrees of self-obsession.

J. Peterman is the epitome of Seinfeldian absurdity, a character almost right out of monty-python. It’s actually amazing that any work gets done at all at his company, given the fact that every brainstorming marketing sessions ends with recounted tales of dancing with tribesmen under the full moon or “fever-dreams in the Peruvian jungle." As far as bosses go, J. Peterman is as absurd as they come.

Verdict: If you can tolerate hyperbolic storytelling, questionable financial decisions and being asked to perform ridiculous tasks while getting no real work done, then Peterman’s a keeper. Don't touch his Urban Sombrero and it will be virtually impossible to get fired. 
 
2. Sid Farkus (The Bra/Manzier Salesman)

Pros: Laid-back office environment, chance to revolutionize brassiere technology.

Cons: An obsession with “the perfect fit” that is definitely uncomfortable.

Farkus has a niche passion - bras. And while his approach might be a little too hands-on, you can’t deny his entrepreneurial spirit and his business acumen by bringing Kramer and Frank Costanza together into an almost successful male bra company. Just don’t bring George into the mix, who is a master at single-handedly torpedoing what could otherwise be a great thing.

Verdict: If you’re okay with working in a highly specific industry and have an affinity for bras (don’t we all), then Sid Farkus isn’t the worst boss - until he gets pushed out for, ahem, inappropriate behavior.


3. George Steinbrenner (A Fictional Version of Steinbrenner - Thank God)

Pros: Free Yankees tickets. You can get away with anything, blame anyone, and he will believe you.  

Cons: Demands ill-advised innovations ("We need a calzone initiative!”). Hires and fires employees on a whim, often for delusional reasons.

The great Larry David’s emmy-worthy portrayal of George Steinbrenner is a legend of lunacy. The tangents he goes off on with George in his office is tv history. The good thing about working for this version of Steinbrenner is that there is pretty much nothing that you can’t get away with as his employee, which is perfects for George.

Verdict: If you enjoy chaos and don’t need job security, Steinbrenner is your guy.


4. Mr. Pitt (Snickers Bar Extraordinaire)

Pros: Elegant lifestyle, cultured conversations.

Cons: You never know when you may have to sacrifice a weekend to help him try on 1000s of pairs of socks in order to find the right fit.

Working for Mr. Pitt means ironing socks and identifying the perfect saltwater crackers. That’s taking a gig as a personal assistant to the next level. On the plus side, you’ll get access to his luxury lifestyle, including watching him eat candy bars with a knife and fork. What a role model! On the downside, you’ll quickly question your life choices.

Verdict: If you’ve ever dreamt of being a butler, Pitt offers the experience without the job title.


5. Rick Levitan (Mickey Recipient)

Pros: Known for his sharp wit and cutting sarcasm.

Cons: Won't hesitate to humiliate you in front of the whole office or fire you for one bad move.

This man is the nightmare of petty bosses. His defining moment? Mercilessly roasting George for putting sugar in his coffee and wearing a sweater vest. Sure, it’s funny when you’re watching it, but imagine being the target. Even George had to resort to slipping him a mickey for revenge. It should be noted that George started their feud by wanting to for once behave in a way that “really gets him canned.”

Verdict: Unless you’re a masochist or enjoy retaliatory office pranks, Levitan is a hard pass.


6. Russell Dalrymple (NBC Network Executive)

Pros: Passionate, creative, and willing to bankroll your bizarre sitcom pilot idea, including shows about nothing.

Cons: Easily distracted by love interests and might abandon the job altogether.

Russell green-lit Jerry and George’’s made up show ‘Jerry’, which shows he believes in outside-the-box creativity. But when things get personal, he spirals - potentially leaving you without a project or a paycheck at the last second. On the good side George meets his late fianceé during his and Jerry’s first network meeting with him. We all know how well that turned out, however.

Verdict: A decent boss unless his heartstrings get tugged or until George is caught staring at his daughter’s cleavage.


7. Mr. Lippman (A Publishing Wizard - Not)

Pros: Runs a respectable publishing company.

Cons: Blames you for everything.

If you dream of working in publishing, Lippman seems ideal, until he finds out you’ve had sex in the office, or if you’ve crossed him in some bizarre way. He may like wooden Indians with cigars for decoration, but he’s a classic and absurd micromanager who’ll throw you under the bus for profit without blinking.

Verdict: Work for him if you can tiptoe on eggshells for years at a time.

 

Winner -  J. Peterman

After reviewing the pros and cons of each of the above caricatures of bosses, if we at Turnkey Office Space had to choose who we would want as our boss, we would go with J. Peterman, simply because working under him gives one the complete freedom to act any way they desire and to get away with it. He’s very easy to fool, not very bright, and is filled with endless stories that will keep you laughing. Who would you choose?