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26 TV Bosses We Either Love or Love to Hate

April 10, 2025 by Talia Ben Itzhak

So many of our favorite sitcoms are based in an office environment with hilarious bosses and side characters who keep you on your toes. Its relatability makes us laugh or cringe, as we all know what working under good and bad bosses is like. Some of these iconic dynamics have been cemented in the list of memorable bosses. Check out our summary to see if you remember any of these good and bad bosses.

#1: Worst: Justin Pitt, Seinfeld

While Seinfeld is ironically based around a group of 30-something year old friends in NYC, Elaine and George have had many memorable bosses throughout the decades, who happened to make our list. Elaine’s bosses were always the most eccentric characters. Mr. Pitt was a control freak with whacky requests. He would take it as far as requesting the right pair of socks! Watching it play out on screens was highly entertaining, but can you imagine working for someone so impossibly controlling?

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Filed Under: Latest, Tv and Movies Tagged With: cheapism, infiniteScroll

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