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Gilbert Gottfried is 40+ years into his career. He’s entertained hundreds of millions of people. And yet, some part of him still wants to be liked.

He was 15 when he started doing stand-up comedy. He dropped out of high school. And within 10 years he was on Saturday Night Live.  

He was big on impressions.

But then he got tired of that. And had to figure out his own act.

Meaning… he’d have to show some version of himself… on stage… in front of an audience.

“I had to develop my own act,” he said.

“What does that mean?”

“I would just go on stage with nothing prepared. And just start talking and joking around. Sometimes, I would lose the audience totally. They’d be walking out. And, back then, I remember I didn’t mind it all that much.”

“Do you think that was an advancement of your skills?” I asked. “Because I’m sure at 15 you were scared to death.”

“Yeah, I mean I think everybody in show business has this split personality where one half of you is like, ‘I’m going into show business and people are going to pay money to come see me because I’m that great.’ And then the other half of you is saying, ‘Oh oh, please love me. Please love me. I want some reassurance that I’m worthy.’”  

“You probably can’t let the audience see you’re nervous about what they think, though, right?”


“Because they’ll tear you apart.”


So he focussed on the act. And the material.

But now the stage is everywhere.

It’s online. It’s on social media. It’s in the hashtags, the clickbait headlines. You can’t leave it at the club or the office or wherever stress used to live.

Now it comes home with you. It’s in your pocket.

I asked Gilbert about this. Because he knows what it’s like to be the center of hate.

He’s made 9/11 jokes, tsunami jokes, jokes about the shooting that happened at the gay nightclub. I asked him about this. He told me about the nightclub jokes.

And why he made them…

He said, “One guy tweeted me and said, ‘I never thought that I’d wake up crying and go to sleep laughing.’ And one other guy sent me a tweet, saying, ‘You make me laugh at times when I don’t want to… and that’s when I need it the most.’”

Some people say, “You went too far.” But Gilbert has a job to do.

He’s a comedian. And if he’s going to keep making people laugh, he has to teach himself how to deal with the half of him that says, “Please like me.”

So I took notes.

Here are the top 3 lessons I learned from Gilbert Gottfried about quieting your insecurities: 



Groupthink is infecting the internet. Every day or week or month, there’s a new “villain.” People get their tweets and stone the villain.

You can spend 40 years building up career. And it can all be taken to trial now by someone in their basement.

I asked Gilbert, “Deep down, what was the worst moment emotionally for you? Where you were at your lowest?”

“Oh god, I don’t remember. I just remember thinking, ‘This is it. It’s all going to stop here.’”

“What would stop? Your comedy career? Would your financial life stop?”

“All of that, yeah. But what I didn’t realize at the time is that the villain of the month is like the flavor of the month at Baskin Robbins. We need someone to go, ‘Hey, come on gang, let’s get a posse together and go after this one.’”

And it’s true. People get excited to join the group and throw punches. They forget that they’re actually hurting someone.

And that the pain can last longer than the tweet. It can bleed into someone’s financial stability, their peace of mind, it can affect their mental health.

Gilbert knows he can’t persuade the team of haters to stop hating. That’s what team they’re on. It’s like trying to convince a Red Sox fan to root for the Yankees.

Red Sox fans are Red Sox Fans.

Yankee fans are Yankee fans.

Hate fans are hate fans.

Don’t try to convince someone to switch teams. Just look for the people rooting you on.

When Gilbert got fired from Aflac (he was the voice of the duck) he saw a lot of hate tweets.

But this one stood out, “Gilbert Gottfried Gets Fired After Aflac Discovered He’s a Comedian.”



Gilbert had a performance a few days after 9/11. It was in New York for the Hugh Hefner roast.

“There were still black clouds floating around,” he said. “The World Trade Center was still burning.”

He got on stage and said, “Tonight, I’ll be using my Muslim name, Hazin binLade.”

Then he said, “I have to leave early tonight…”

And this is where he lost the crowd.

He said, “I have to go to LA. Unfortunately, I couldn’t get a direct flight, we have to make a stop at the Empire State Building.”

“People were booing and hissing. Chairs were screeching back. And one guy yelled out ‘Too soon.’”

I appreciate any kind of humor. But this was so extraordinarily crude, I almost didn’t want to laugh. But I’ve learned that’s when I need to laugh. Because, if I don’t laugh, I’m choosing misery over freedom.

I’m trapping the toxin in my blood. And not giving myself a chance to grieve or move on.

When Gilbert heard, “Too soon,” he got confused.

“I thought that meant I didn’t take a long enough pause between the setup and punchline.”

“You assumed the audience were all professional comedians?”

“Yeah,” he said laughing. “If you said I was up there for 200 years after that joke, I’d believe it. That’s what it felt like.”

Gilbert was gripping the podium. He stood back. And if you watch the video, it looks like he’s lost.

“What was going through your mind?”

“I figured I already lost the crowd, why not go to the bottom level of hell?”

He went deeper and deeper into his act.

“And then they started laughing and applauding and cheering. And it just showed that they needed that release.”

Tension is everywhere. It’s in our families, our relationships, our work. It’s in our fears. Gilbert sort of has this gift to look past the miserable.

I wish I had that gift. But I don’t. Sometimes I get stuck. And that’s when I need laughter the most.

Gilbert could’ve walked off stage. And left feeling like he’d lost.

Maybe that’s what the crowd would’ve wanted. Maybe they would’ve wanted to see him leave and say, “Yay, we did it. We destroyed him. He’s gone.”

But he didn’t give them that opportunity. He went to the bottom. And rose up from there.



Whenever someone tells Gilbert not to joke about something, he jokes about it.

He gave me an example.

He said, “How do you make a dead baby float?”

“…a glass of ice cream, two scoops of dead baby.”

I didn’t get it. But his delivery was funny.

Some people are against “dead baby jokes.” It’s against their moral compass. But Gilbert isn’t saying “I approve of a baby dying.”

“When you’re doing those jokes, you know it’s horrible,” he said. “That’s why you’re saying the jokes. Because it’s so awful.”

Part of it is temptation.

If you’re in school and the teacher tells you to be quiet, don’t you want to make noise?

People tell you, “Don’t do X.” They say it because someone else told them “Don’t do X.”

So if they see you do X, it’s just proof that they’re in chains. And that they followed a rule that doesn’t actually exist.

They realize they made a choice. And they didn’t want to make that choice.

Which causes regret.

And regret is painful.

So people keep saying, “Don’t do X” to prolong the pain.


Gilbert is always going to have some piece of him that wants to be liked. But it’s getting smaller and smaller.

At first, he was half “please like me” and half “I’m the greatest.”

Now he’s some part “please like me” and some part “I want to make you laugh. I want to help release the tension.” And he’s some part “I want to have fun at what I’m doing.” And another part “I want to improve at my skill.”

People are always going to be outraged. News moves fast today. And it’s easy to get outcasted.

It’s another thing to fall down.

Gilbert didn’t let Aflac become a death sentence. Instead, he laughs at the absurdity.

“When people get offended and outraged, they’re patting themselves on the back,” he said. “They’re like, ‘See, I was outraged!’”

There’s no award for getting angry. And there’s no award for surviving the Twitter mob.

There’s only reward in deciding you’re more than just half and half.