Work plays a huge part in our lives, and most people will be able to remember the good bosses and the bad bosses that they’ve had in their lives. Whether you work in an office with executive desks or with members of the public, you know how important it is to have a great boss.
Since the internet is awash with both fictional and real-life examples of terrible bosses, we’ve asked the writers at The Book, The Film, The T-Shirt who they thought were the funniest bosses on TV.
Ted Lasso – Ted Lasso
Ted Lasso was a rare sunny spot during lockdown in the UK. As we all stayed in and binge-watched, word spread of this little-known Apple TV+ show about an American brought over to run an English Premier League team.
Though the show did deal with some weightier themes, the lovable Coach Ted worked his way into our hearts with his sense of humour, aw-shucks humility and supportive coaching style. He also makes biscuits too.
Raymond Holt – Brooklyn 99
When Captain Raymond Holt was brought in to run the 99, he was positioned to be the uptight, rule-following boss that cramped the crime-fighting style of Peralta et al.
Holts’s deadpan delivery and fastidious approach to almost everything was a masterclass by Andre Braugher. Of course, over the course of Brooklyn 99’s run, Holt wins the respect of his team and he would do anything for them too. From the annual squad Halloween heist competition to his ongoing feud with Kyra Sedgwick’s Madeline Wuntch, Holt got laughs in every scene. And all this while also raising themes of racism and homophobia within the NYPD.
Montgomery Burns – The Simpsons
If Monty Burns was a character in a live-action series, he’s been on the worst bosses list. After all, some of the things he’s done have been horrific. Voiced by Harry Shearer, Burns is an old-school villainous billionaire of the corporate class, who is as deliciously hilarious as he is cruel. Excellent.
Dr Perry Cox – Scrubs
From the day that JD, Turk and Elliot set foot in Sacred Heart hospital, the hilariously brutal Perry Cox has been on their case. His manic sarcasm and unrelenting hatred of Hugh Jackman made him one of the funniest on the show. However, instead of being a big bad boss to be feared and hated, John C. McGinley’s Cox was one hell of a doctor, advocating for his patients, breaking the bureaucratic rules to help people and being an excellent doctor. The comedy came from many fronts. His battles with hospital boss Bob Kelso and the sparring with his ex-wife/current partner Jordan running alongside his mentorship of the young doctors.
Michael Scott – The Office (US) & David Brent -The Office (UK)
Whether you’re a fan of the Ricky Gervais original or the US remake. David Brent and Michael Scott have entered the pop culture lexicon of funny yet terrible bosses. Both completely self-obsessed and incompetent, they both carefully walked a line between becoming completely hateful and misunderstood. Steve Carrell played Michael Scott as more irritating and high energy while Brent was Gervais’s signature style or awkward, uncomfortable humour.
So there you have it, our team’s funniest TV bosses. There are so many more that could be on this list, drop us a comment below and tell us who you would add to this list.
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