Welcome to Dead Mentor.

Come on in, look around and stay a while.

Tap Into Your Dark Side for Humor Like Robin Williams

Tap Into Your Dark Side for Humor Like Robin Williams

If being funny doesn’t come to you naturally, then you have to actively tap into it. Mine your dark side like comic legend Robin Williams did to unearth and unleash comedy gold.

One of my favorite Robin Williams jokes is so wrong, but also so right on so many levels that it could have been born out of no place other than total darkness. It goes like this:

“I was once on a German talk show and this woman said to me, ‘Mr. Williams, why do you think there is not so much comedy in Germany?’ And I said, ‘Did you ever think you killed all the funny people?’”

For Williams, the rapid-fire comic firebrand, this was ostensibly an effortless, on the spot dark comedy riff that at once spoke to the horrors of the Holocaust, humorously stuck it to an entire nation and answered this poor woman’s innocently asked question with hilarity and comic panache. 


Perhaps no comedian was more gifted at plunging to the depths of darkness—more often than not his own—to find jokes than Williams. In fact, based just off his dark humor jokes alone, you could easily ascertain that his childhood years were filled with loneliness, the shame he felt of being overweight, the torment of being bullied and the crushing depression that went along with all of it. 

Save for his wild success as an entertainer, his adulthood was no improvement. Williams battled the demons of alcohol, drugs and continued depression while experiencing marriage after marriage crumble, in part due to his serial infidelity, but mostly due to his overall horrendous sense of self-worth. As author David Itzkoff puts it in his intriguing and exhaustive biography, Robin:

“The real Robin was a modest, almost inconspicuous man, who never really believed he was worthy of the monumental fame, adulation and accomplishments he would achieve.”

So was Robin Williams a brilliant comedian simply because his life was filled with such pain and as a result, he was rich with such dark source material? Of course not. He had the kind of rare and brilliant comic mind that could have (and did) turn nearly anything into a punch line. But a big part of his success was the fact that he was willing to go to that place where he could find things within himself that were seemingly too wretched and painful to share. And then turn them into absolute howlers.

So this brings us to you. 

Are you an effortless humorist? Do you kill everyone you meet with an endless repertoire of jokes? Are you tuned into some divine frequency that funnels one-liners directly into your brain? If you answered “yes” to any of these questions, then read no further because you’re already comedy light years ahead of most of us.  

However, if you’re not strolling through life like the world’s your own personal stand-up comedy club, then know this: studies have shown that one of the brain’s most effective ways to handle dark, dangerous, uncomfortable and bizarre ideas, like death, war, addiction and suicide to name a few, is with laughter. 

That’s why Williams and some of history’s funniest comedians routinely delve into the seedy underbelly of their lives to find dark humor jokes that will make you laugh maniacally (and cringe and cry, as well).

Let’s take a look at some of the jokes Robin Williams had to wade into his dark side to find, so he could fuel his comic voice. And while we’re at it, let’s see if we can inspire you to do the same.

Face Your Deepest Insecurities 

“I had my back waxed by two women… and at one point they said, ‘Do you mind if we take a break?”

If there was one thing Robin Williams was known for, it was being funny. If there were two things he was known for, it was being funny and hairy. 

This joke works so well because it comes from a place of facing insecurity head-on and putting it on display for all to see. Williams cracked wise time and again about his hirsute body and what a misery it was for him, especially during his youth. So much so that in later years, he was known to sport a more manscaped look. Here, he hilariously reminds us that not only is it humiliating to have too much body hair, but even the process of having it removed is a total embarrassment.

What less-than-flattering physical trait do you have? What have you done to hide it, change it or rid yourself entirely of it? It’s time to get brave and funny about it and, finally get the laughs you deserve. 

Find Dark Humor Jokes in Your Failed Relationships

“Ah, yes, divorce… from the Latin word meaning to rip out a man’s genitals through his wallet.”

Robin Williams was married three times. His first two marriages ended in divorce. It’s been reported that he paid out north of $30 million in alimony over the course of his lifetime and he even talked about, as a result, having to sell his estate in Napa because he could no longer afford it. In this great joke, he creates his own definition of divorce, as it applies to his financial situation, and paints a strikingly vivid picture of what it feels like to endure it.  

If you really want to be funny, open up your former romantic relationships to us and let us all see what a disaster they were. If your relationship was a colossal financial mistake, even better—who can’t see the humorous side of a person who got married without a prenup because they were “in love” and then got taken for half of everything? 

Plus, we’ve all made our own relationship mistakes so knowing the hilarity of yours will only make us bond through humor with you that much more. The bigger the relationship blunder you committed, the riper for laughs it is. 

Reveal Your Shame

“I had sex with a prostitute when I was 21. It was so bad, she gave me a refund.”

If you’re one of those people who can’t laugh at yourself, then study this joke closely—blatant self-deprecation is one of the easiest paths to getting chuckles. While this could easily be a made-up joke, since we know a bit about Williams’ lifestyle and behavior, let’s assume that it’s based on a true story. And the way Williams does it here, not only shining a spotlight on the fact he had hired a sex worker, but that he also epically failed to perform, works like a charm.  

This joke is a great lesson in the fact that the things in life you feel the most shame and embarrassment about are going to result in the best jokes. Why? Because they give us a window into your private world, they humanize you and they remind us of our own embarrassments. Tap into that and I guarantee you’ll have our undivided laughter. 

Embrace the Truth

“I am one of the luckiest f**ks in show business — with the possible exception of Ryan Seacrest.”

Robin Williams once said, “In the process of looking for comedy, you have to be deeply honest.” This joke works because it uncovers a real truth: you have to get lucky to be successful. A lot of successful people don’t want to admit this. They think they made it on talent and talent alone, or at least want to project that notion. 

Yes, Williams is arguably among the most talented comedians in history. Yes, he did some killer stand-up routines. And yes, he made some great movies. But he also got plucked off the street (literally) by producers at a young age to play a space alien on TV. Without that happening, there might have been no Robin Williams.

By the way, I used to have a philosophy that celebrities should only poke fun at celebrities above them on the career food chain, not below. But in this case, I’m good with it.

So anyway, find the cold, hard truths in your life that most people are afraid to admit and admit them in the form of a joke. You’ll not only make us laugh, you’ll also earn our respect.

Your Loss is Your Audience’s Gain  

“Cocaine is God’s way of saying that you’re making too much money.”

If getting your money taken away by your ex-spouse is funny, then blowing it (pun intended) on your own is absolutely hysterical. 

On the one hand, Williams makes himself sound like a buffoon here for being so stupid and reckless with his money. On the other hand, he uses his dark sense of humor to inject the joke with a degree of pathos by invoking the elements of addiction and the dangers of abundance.  

Think about what you once had that was so great and then lost via your own unchecked addictions, indulgences or just plain neglect. Money? A significant other? A healthy body? A job? Whatever it may be, your loss is an epic joke waiting to happen.

No matter who you are, you’ve lived a life filled with at least some unfortunate events, blunders, defeats and darkness. Don’t let them go to waste. They’re ripe for fueling the humor you want to project to the world. 

Now go write an epic dark comedy joke about yourself and make someone fall off their chair with laughter.


Be True to Your Own Spirit Like Jim Morrison

Be True to Your Own Spirit Like Jim Morrison

Control Your Emotions Using BKS Iyengar Yoga Techniques

Control Your Emotions Using BKS Iyengar Yoga Techniques