Does the word 'boss' have a negative connotation only?
In many video games and movies I've played ever, I often saw a lot of characters calling his superior as 'boss'.
I don't have any particular questions about it until now, but I'm starting to wonder how it feels when you hear someone calling you a boss.

I've searched for this word on google, the first thing I saw was 'managing your boss'. Yes. I know someone might not want to be called that, as in 'He's too bossy'. But I think that's not the only thing that has.

What's the first image that comes to mind on hearing the word 'boss'?
Negative, value neutral or depends on the situations?

* Edited some typos.

Question

Does the word 'boss' have a negative connotation only?
In many video games and movies I've played ever, I often saw a lot of characters calling his superior as 'boss'. 
I don't have any particular questions about it until now, but I'm starting to wonder how it feels when you hear someone calling you a boss.

I've searched for this word on google, the first thing I saw was 'managing your boss'. Yes. I know someone might not want to be called that, as in 'He's too bossy'. But I think that's not the only thing that has.

What's the first image that comes to mind on hearing the word 'boss'?
Negative, value neutral or depends on the situations?

* Edited some typos.

Answer

It's not negative at all. It's a fairly neutral word, and if you hear someone calling their superior 'boss', this is likely to suggest that they have a friendly or even informal relationship.

The only negative association is the adjective 'bossy', used to refer to someone who has a pushy, domineering  manner. But this is only because the person who is behaving in a bossy manner ISN'T your boss - they might be your sister or brother, wife or husband, for example. That's why it's negative.

What image does 'Boss' suggest? Bruce Springsteen, of course.

Answer

Hi! That's a really good question. It's really depends on the situation and context. If you're simply talking about your superior at work, it generally has a neutral conotation. Of course, like you brought out, no one likes to be called bossy. It's also interesting to note that sometimes in slang (at least in America) it can mean something good. It's kind of older slang but sometimes i still hear it. When something is described as "boss", as in "that car is so boss", it can mean "cool" or "top notch". Hopefully that's helpful. :)

Answer

I'll add that in America sometimes men will call a male friend 'Boss' as in, "Hey Boss, what's up? This is simply our way of saying friend or pal or something of that nature. It's a little hard to describe.

Answer

For me, "boss" is neutral or positive! If I call my supervisor or superior my boss, that is neutral, since it is just describing our work relationship. If someone calls me a boss, it's positive and means they respect me and the quality of my work!

In the situations where "bossy" is negative, it's usually because the person being described is acting like a superior when they don't have any actual authority (like when kids tell each other what to do).