13 Hall of Fame Jokes About Bosses

Jokes about the person that doesn’t know you’re reading this right now instead of working
13 Hall of Fame Jokes About Bosses

Going to work sucks. We know this and hate it, too; after all, it’s a universal loathing. And usually the main reason why work sucks is due to your boss. The person who makes all the decisions and makes you do them. The person who underpays you. The person who makes you wonder how the hell they even got to the position they’re in. 

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Luckily, though, there a number of comedians who have become their own bosses by telling jokes about their previous employers to lighten our despair. And so, to help get the Mondays out of your system, we’ve rounded up some Hall of Fame jokes regarding your in-office overlords...

The Awkwardly Aggressive Job Interview

In this Saturday Night Live sketch, Steve Buscemi is an angry boss who just can’t seem to understand anything on a resume. The applicant should have gone to Pepperdine.

Kids in the Hall Point Out the Obsessiveness of Bosses

Toys ‘R’ Me

The late Lance Reddick brings a hilarious, militant delivery as the boss of a chain toy store. We salute and miss you, good sir.

Like a Boss

Just a standard performance review, nothing more.

Undercover Smurf Boss

Robot Chicken highlights the issues of working for Papa Smurf — including the problems of garbage health care being tied to employment. Even woodland fantasy creatures have high deductibles!

Ilana’s Intern Abuse

On Broad City, Ilana creates an intern army and grows mad with power, just like anyone with an unpaid workforce would.

Key & Peele’s Possibly Non-Existent Boss

Mr. Mahina is a real, real person. For real. For true.

Mr. Burns’ Bee-Sting Solution

On The Simpsons, Mr. Burns saves his loyal lacky Smithers from an allergic bee sting the only way he knows how — by bossing him around.

Tom Green’s Boss: Donald Trump

Green went on Comedy Central’s This Is Not Happening to discuss his time on The Celebrity Apprentice, in which he had to work for Donald Trump and got fired on national TV for hanging out with Dennis Rodman.

Ian Bagg Roasts the Boss and an Intern

Bagg does some crowd work and discovers a scared intern in the audience. After some needling, he finds out his boss is in the crowd, too.

Maria Bamford’s Annoying Lady Boss

“Sometimes it’s hard to work for a lady boss, especially when she tries to act like she’s your friend. She calls you ‘honey’ and ‘sweetheart,’ and ‘Girlfriend, heeeyyyyyy! I want you to take a break, take a walk, get me a latte, and it’s 2-percent milk; you should know that by now, hahaha.’”

Bill Lumbergh: Boss MVP

The epitome of a bad passive-aggressive boss is Bill Lumbergh from Office Space, the modern template of villain bosses in the 1990s going into the modern era. Thankfully, the rise of remote work can allow men like him to die off as they should.

‘SNL’s Evil Boss

As a very bad-tempered boss, Will Ferrell unleashes such great mock rage that even Pierce Brosnan couldn’t hold it together.

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