National Bosses’ Day: Best & Worst On-Screen Bosses

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Celebrate Boss's Day on October 16th, 2015!

October 16th is National Boss’s Day!

Whether you love or hate your boss, you have to admit it’s a tough job. In honor of Boss’s Day, here’s a list of the most memorable bosses, good and bad, on the screen.

Best Bosses:

Jack Donaghy

Jack Donaghy (30 Rock) – Though Jack may have a tough exterior, he always had Liz Lemon’s back. Watching his mentorship with Lemon evolve was never without a laugh, and he became even more endearing when he showed his flaws.

Kermit (The Muppet Show) – You have to give props to the little green guy who’s been leading the jovial Muppets since 1955.

James T Kirk

James T Kirk (Star Trek) – Navigating the USS Enterprise and its crew through space, the final frontier, and to boldly go where no one has gone before.

Don Draper (Mad Men) – The toughest boss to please of all, but he gets results.

Jimmy Dugan (A League of Their Own) – Here’s another boss that’s tough on the inside but a total sweetheart in the end. There may not be any crying in baseball, but Jimmy brought the league to the World Series.

Ron Swanson

Ron Swanson (Parks & Recs) – When his only interests include whiskey, meat, and woodworking, it’s easy to shop for a boss like Ron Swanson. Though he’s a walking contradiction (a government worker who distrusts the government), he always lets his staff shine and gives them credit when it’s due.

Annalise Keating (How to Get Away with Murder) – Don’t get on her bad side, because she has a lot to teach you.

Captain Raymond Holt (Brooklyn Nine-Nine) – His personality and his humor both dry, but it’ll make you want his approval even more.

Charlie Skinner

Charlie Skinner (The Newsroom) – Journalistic integrity is his number one mission, and he’ll go to the depths of the earth to protect it and his staff.

Worst Bosses:

Horrible Bosses

All of the bosses from Horrible Bosses – Literally all of them.

Bill Lumbergh (Office Space) – No one wants to come in on a Saturday or do those TPS reports. No one.

Franklin Hart, Jr. (9 to 5) – Heartless Hart would do anything to take his staff’s ideas and take credit for them.

Frank Costello (The Departed) – No one likes a rat. Especially a boss rat.

Montgomery Burns

Montgomery Burns (Simpsons) – There is no evil like Montgomery Burns evil.

Nucky Thompson (Boardwalk Empire) – Nucky is another guy who only cares about the bottom line, no matter who he hurts.

Dick Jones (Robocop) – Greed and corruption take over the town of Detroit, and Dick Jones only cares about the bottom line.

Miranda Priestly

Miranda Priestly (Devil Wears Prada) – How far is too far to prove a point?

Emperor Commodus (Gladiator) – Immoral and jealous, Commodus will kill anyone for his gain.

Michael Scott

Bonus Boss: Michael Scott of The Office. It’s hard to say he’s the best or worst. As difficult as it would be to get actual work done when he’s around, the workplace just isn’t the same without him.

Show your appreciation for your boss with the list of gift ideas featured on Amazon.

The easiest way to show your appreciate is with a mug! Here are some fun mugs for your boss to start off the day:

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