15 of the Best (and Not-so-Good) Boss Characters


Whether or not we realize it, there is kind of a “holiday” (in the loosest sense) for nearly everything. From locations to our favorite foods, there’s a silly holiday set aside to encourage its epicness. On this day, it’s national boss day, which means it’s time to celebrate some of the best boss characters. Or at least highlight those who are memorable as not all of them I’d call “the best.”

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As I was thinking through this list (last minute because when am I ever ahead of the list-making game?), I tried to run up a list that was a bit more varied than the usual “boss character” that immediately comes to mind. These would often be law enforcement characters since I watch a heck of a lot of crime dramas. With that in the forefront of my must-get-this-written brain, I set out to create a list with an range of different personalities, and workplaces.

I’ll be honest until recently I’ve seen very few workplace comedies, and even now, I still don’t watch that many. Of the workplace comedies I watch, I think I can confidently say, there’s very few bosses whom I really “like.” That said, this doesn’t mean they aren’t memorable. While not everyone on this list is really likable, they certainly do make an impression.

15 of the Best Boss Characters for National Boss Day

1: Mike Baxter

Where you know him from: Last Man Standing (ABC, now Fox TV comedy)

Thoughts: I had to add Tim Allen’s Mike Baxter to the list. He’s a hilarious character, and there’s a boatload of scenes that take place at his workplace.

2: Jason Bull

Where you know him from: Bull (CBS TV drama)

Thoughts: This is an interesting character study because while Bull is quite likable, he’s really also quite messed up. He excels at what he does professionally (as a trial scientist) but personally? Yeah, he’s kind of a wreck.

3: Mary Fiore

Where you know her from: The Wedding Planner (2001 feature film)

Thoughts: To be honest, I’m not sure if Jennifer Lopez’s Mary fits on this list or not. I’ve seen this delightful romantic-comedy a million and one times, but cannot remember if she owns the wedding planning business or works at one. Either way, I admire her character and the moral stand she takes against the possibility of being with her person.

4: Miss Phryne Fisher

Where you know her from: Miss Fisher’s Murder Mysteries (Acorn TV mystery series and novels penned by Kerry Greenwood)

Thoughts: In reality, Phryne isn’t a boss in the way some of these other characters are, but I’m still calling her a legit boss, because, she has all the qualifiers, plus she’s fearless.

5: Leroy Jethro Gibbs

best boss characters

Where you know him from: NCIS (CBS TV drama)

Thoughts: Gibbs is one of those characters who verbalizes very little, but can say so much in how he acts, treats others and protects his team, and those who mean the most to him. Needless to say, he’s one of the best things about this long-running drama, and I love how protective he is.

6: Lorelai Gilmore

Where you know her from: Gilmore Girls (CW TV dramedy)

Thoughts: Lorelai isn’t always her own boss, but eventually she becomes one, and it’s about the most cozy thing ever considering she runs a quaint inn, plus her best friend works with her as a partner, so there’s that too – and I just feel like I haven’t talked about the Gilmore’s for a hot second.

7: Dorcas Lane

Where you know her from: Lark Rise to Candleford (BBC seires)

Thoughts: I mean, who doesn’t like Dorcas? She’s tough when necessary, but the girl has a heart of gold.

8: Daniel Meade

best boss characters

Where you know him from: Ugly Betty (2006 ABC comedy)

Thoughts: Again, Daniel is far from perfect. But what can I say? In the seasons I’ve seen (so far), I kind of have a soft spot for this guy. Still, he’s not exactly a poster boy for “best boss ever,” because let’s be real, the dude misses a lot of work, like, get it together, Daniel.

9: Ned

Where you know him from: Pushing Daisies (2007 ABC comedy)

Thoughts: Aww, Ned! This is one good egg character. Love him.

10: Jules Ostin

Where you know her from: The Intern (a 2015 feature film)

Thoughts: This is one of those movies I don’t remember specifics of, but do remember being impressed by the Nancy Meyers comedy. Anne Hathaway plays a young CEO, and unlike The Devil Wears Prada, she plays a good boss.

11: Oliver O’Toole

Where you know him from: Signed, Sealed, Delivered (Hallmark Channel signature mysteries movie series)

Thoughts: I mean, who doesn’t like Oliver? He’s just that cool albeit in an old-fashioned way. (Also, yes, Eric Mabius plays this character, who played Daniel Meade!)

12: Miranda Priestly

best boss characters

Where you know him from: The Devil Wears Prada (a novel, and 2006 feature film)

Thoughts: Speaking of The Devil Wears Prada! Ok, so this is one of those characters I cannot really say I like, but she 100% does make an impression. She’s fierce, opinionated and knows what she wants in business (and in some ways, I think having known Andy, she does grow – a little bit). Also, Meryl Streep just plays her to absolute perfection.

13: Tony Stark and Pepper Potts

Where you know them from: Iron Man (a 2008 feature film) and the MCU films

Thoughts: Tis true, Tony might not be the most empathetic boss, but one has to admit, he does have great success when it comes to business. He’s not only a brilliant inventor, he’s also got a successful company called Stark Industries. I also cannot neglect Pepper because a: she’s brilliant and b: she does run the company… a lot!

14: Margaret Tate

best boss characters

Where you know her from: The Proposal (a 2009 feature film)

Thoughts: Again, no, Margaret isn’t the “best boss,” but she does grow, and one has to admire her business savvy (plus I’m pretty sure Sandra Bullock makes her SO much more likable than the character is).

15: Detective Mac Taylor

Where you know him from: CSI: NY (CBS TV drama)

Thoughts: Mac is a tough, but very fair boss as the head of the New York crime lab. He does have to fire some people, and reprimand them, but it’s always with reason, and because he holds his lab, and himself, to the highest of standards (to ensure their important work is above second guessing).

Additional Boss Characters Include: Cat Grant (Supergirl); Jessica Pearson (Suits); Dwayne Pride (NCIS: New Orleans); Bruce Wayne (Batman); AND MANY MORE!

15 of the Best (& Not-so-Good) Bosses For National Boss Day. Talking about the best boss characters (and the not-so-good ones, too). #NationalBossDay Click To Tweet

Tell me, which characters would you put on a ‘best boss characters’ list? Do you have a list of favorites? Have you met any on this list; do you like or dislike them – and if so, why? Comment all of your thoughts down below.

Thank you for visiting!

About Rissi JC

amateur graphic designer. confirmed bookaholic. bubbl’r enthusiast. critical thinker. miswesterner. social media coordinator. writer.


  1. Ooh, you mentioned some of my favorites on here. This list is especially interesting to me since I’ve never actually thought of these characters in terms of being bosses, even though they are.

  2. Great list. I recognize most of them.
    As long as we are at it: Commissioner Frank Reagan of Blue Bloods.

    1. OHMYGOSH! YES. I love Frank Reagan’s character, and someone mentioned him on Twitter, too; his name should have been on the list, but alas, I overlooked him when I finally put it all together. Next time I guess! :D

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