· 2 mins · Management Skills

10 of the Best and Worst Bosses in TV and Film

In honour of National Boss's Day, we've rounded up some of the most horrific and inspiring (fictional) bosses.

Avatar of Shannon Maloney Shannon Maloney

It’s October 16th. But more importantly, it’s National Boss’s day and we’ve rounded up some of the best and worst bosses from tv and film. Keep reading for our list of exceptionally terrible and surprisingly successful leaders:

The Best Bosses 🏆

1. Captain Raymond Holt, Brooklyn 99

Great boss qualities: Direct, transparent, delegates responsibility

“Every time someone steps up and says who they are, the world becomes a better, more interesting place. So thank you.”

Photo credit: Pinterest.com

2. Leslie Knope, Parks and Recreation

Great boss qualities: Motivating, cheerful, optimistic, creative

“There’s nothing we can’t do if we work hard, never sleep, and shirk all other responsibilities in our lives.”

Photo credit: Giphy.com

3. Albus Dumbledore, Harry Potter

Great boss qualities: Inspiring, humble, respectful

“It is a curious thing, Harry, but perhaps those who are best suited to power are those who have never sought it.”

Photo credit: Giphy.com

4. Captain Jean-Luc Picard

Great boss qualities: Patient, inquisitive, decisive

“Things are only impossible until they are not.”

Photo credit: Variety.com

5. Miranda Bailey, Grey’s Anatomy

Great boss qualities: Honest, straightforward, compassionate

“Never be afraid to stand up for yourself. Just be sure you are right when you do.”

Photo credit: giphy.com

The Worst Bosses 👎

6. Michael Scott, The Office

Bad boss qualities: Offensive, selfish, distracting

“Do I want to be feared or loved? Easy – both. I want people to be afraid of how much they love me.”

Photo credit: winkgo.com

7. Miranda Priestly, The Devil Wears Prada

Bad boss qualities: Demeaning, demanding, deceptive

“Please bore someone else with your questions.”

Photo credit: vanityfair.com

8. Mr. Burns, The Simpsons

Bad boss qualities: Greedy, dishonest, devious

“Family, religion, friendship. These are the three demons you must slay if you wish to success in business.”

Photo credit: yahoo.com

9. Darth Vader, Star Wars

Bad boss qualities: Vengeful, angry, combative

“Be careful not to choke on your aspirations.”

Photo credit: Cinemablend.com

10. Principal Trunchbull, Matilda

Bad boss qualities: Evil, scornful, terrifying

”It makes me vomit, to think that I am going to have to put up with a load of garbage like you in my school for the next six years.” 

Photo credit: Giphy.com

Celebrate national boss’s day with a shoutout to all the #bestbosses you’ve had on Twitter. 👇

Want to know which fictional boss represents you best? Take this fun quiz!

What you should do next

Now that you've read this article, here are some things you should do:

  1. You should check out our YouTube channel for more tips on management skills and team building.
  2. Check out Hypercontext to see how it can help you run a high performing org.
  3. If you found this article helpful, please share it with others on Linkedin or X (Twitter)

Hypercontext Logo helps managers run better Meetings edit_calendar , hit their Goals flag , and share better Performance feedback insights , faster.

Learn more (it's free!)