Are the funniest people often the saddest?

I would say so - humor is so often a defense mechanism against depression. Robin Williams is only the most recent example of comedians who self-destructed in one way or another because of deep and incurable depression. People like Gilda Radner, John Belushi, Richard Pryor and countless other nationally-known comedians had long struggles with depression, and in the case of Pryor and Belushi, they tried escaping through drugs and lost their lives in full or part due to drugs.

Some of the funniest people I've known personally used humor as an escape from depression - and so have I. My dad died when I was four and in many other ways I had an unhappy childhood, and I obsessively sought out humor in my life as a way of feeling better. It wasn't an ideal coping mechanism, but better than others I've tried.

Look, the funnies people are the saddest. The kindest are the most lonely. The ones who smile at inappropriate times are the ones who have the most problems. The ones who make fun of people a lot are the ones that are jealous or have many life problems and they want to hide it by making fun of people.

Some of the funniest people you see are often the saddest, it's not like they want to be or that they choose to be it's that life is cruel and they use their humour to defend from feeling that sadness. I also think that if someone is funny and they can make others smile and show them happiness they are protecting themselves from their own demons, to cover their own hurt and sadness with humour so no one knows about how deeply hurt they are by anything causes more sadness.
Depression and sadness is a cycle and it is a downward spiral of emotions and actions, if someone who hides this with humour is around and no one notices how hurt and aching and sad this person is then they will never receive help or guidance, they will constantly be in this cycle of pain.

Yes

Yes - quite often.
People expect a comedian to be funny ALL the time.
And good comedy is the hardest form of acting or performance.
The pressure is enormous, success is rare, and many great comedians just can't deal with it.

Attitude, be it humor, a loud voice, snide remarks, are defense mechanisms people use to keep their privacy, kinda like keeping people at bay so they don't ask too many questions. Funniest people are similar and to keep their balance, they make people laugh and entertained preventing any digging into their own loneliness or sadness. I think of Robin Williams, so loved for his humor and yet saddest in how he went.

Funny people are just like any other individual. They have their ups and downs. People who enjoy making others laugh get a high from it. A sense of accomplishment or fullfillment that i made someone else feel good. Of course when things are down for them they do not relish in the same glow as when they are happy. Overall the prankster is often forgotten in other emotions by individuals so people turn a blind eye to their problems. I think this can attribute to loneliness for the individual when they need support such as the case of robin williams.

We often find that people who are funny or have a sense of humor are indeed very sad. This is because humor is one of the many ways that people mask their feelings. It's like how if someone gets angry all the time when negative things are said to them, its a coping method to not show their sadness. Even though it is extremely common, it's not healthy for anyone to simply mask their unhappiness with other emotions. Whoever you are thinking about when you ask this question, I wish them the true happiness that makes others laugh when you speak to be given to you.

The saddest--are you comparing it with funny or just what you hear in the pipeline? I don't understand what you mean by funniest. You mean like, the most perceptive, the most honest, the most sympathetic, the most animated? People who are 'funny' to us can change the world with a smile. If one of them were to take life so seriously as the more uptight and unemotional, the morose, sure they are the saddest. Because misery loves company.

Yes, they are. They're also often tortured souls and struggle with their sanity. Those who are great at comedy are brilliant and their mines race with genius. Unfortunately, the neighbor of genius is insanity so this makes them sad.

Robin Williams was my favorite comedian. He was brilliant without a doubt. I can see why he struggled with the pain of sadness of being so talented. Someone once told me that it's a lonely and sad place to be when you're brilliant. I know he was right. And I know this is some of what Robin Williams struggled with.

Anything that's extreme means there's a problem in some way. That includes genius.