Skip to main content

Greg Giraldo on Failure

By September 30, 2010October 16th, 2020Uncategorized
Greg Giraldo

Photo: Dan Dion

In May 2009, I had the privilege of interviewing Greg Giraldo, the brilliant comic who died yesterday at age 44. I owe that honor to my friend Joey Gay, who persuaded the normally reclusive Giraldo to talk to me for a series of celebrity interviews I was doing for a cover story in Psychology Today.

Giraldo’s intelligence and wit were apparent throughout our conversation, but what struck me most was the way he saw himself. “I feel like I’m ‘the piece of shit at the center of the universe,'” he told me. “The reality is I’m not a ‘get knocked down and come back harder’ kind of guy.”

As someone who loved his work, it made me sad to hear him being so hard on himself. And in trying to fathom his death yesterday from an overdose of prescription drugs, it’s hard not to connect it to the self-loathing that was on display during our interview. One of his answers in particular stayed with me:

“I’m a total fuckup, honestly. And I’ve fucked up a lot of things in my life. I’m constantly tortured by a sense of failure. I feel like hiding in drugs or alcohol. I feel like quitting all the time.”

This is the second time I’ve interviewed a brilliant comic who’s passed away soon afterward. In 2008, I spoke to George Carlin just nine days before he died in what turned out to his last interview. Like Carlin, Greg Giraldo was a genius and an iconoclast. He will be missed. —Jay Dixit

What have been your greatest failures?
It’s hard to distinguish when I was actually struggling from when I only felt like I was struggling—which was pretty much always.

You went to Harvard Law School then dropped out. Tell me about the decision to quit.

It was scary. I had a lot of student debt and I didn’t know where the career was going. I started doing comedy for the hell of it and I thought, “I’ll pursue that somehow until I figure out what I’m actually going to do for a living to pay my loans.” I didn’t think comedy was a viable career option.

But before I quit, I was dying. I mean, I couldn’t do it. It wasn’t like I was a functioning professional and I just made the choice to throw it all away to pursue this crazy dream. I was incapable of being a lawyer. It wasn’t an option. I was going to stop being a lawyer whether I wanted to or not.

How did you feel?

My family was disappointed. But I always wanted to do something creative. I’ve always had real trouble knowing what my actual desires and goals are. I’ve just been dragged along by fate. I can’t even tell you why I thought to go to law school.

What do you think it is about your personality that gives you your sense of purpose?

I’m a total fuckup, honestly. The reality is I’m not this person with this driving “get it done” attitude. I’m a complete fuckup and I’ve fucked up a lot of things in my life. I’m constantly tortured by a sense of failure. I feel like quitting all the time. I feel like hiding in drugs or alcohol. I feel like I’ve failed in terms of what my potential is. I don’t think I’ve achieved my potential because I haven’t worked that hard and I haven’t found the right angles. The reality is, I’m not a “get knocked down and just pull myself back up by my bootstraps and come back harder” kind of guy.

“It’s a lot of self-hatred. That I should have gone to L.A. for pilot season. That I should have drank a lot less.”

What’s that like, that feeling of being tortured by failure?

It’s a lot of self-hatred. That I should have gone to L.A. for pilot season. That I should have drank a lot less.

There’s all these things I’ve fucked up. If I had only stayed focused, I would have been further along. It’s this constant feeling of not having achieved enough.

What do you do about it? Is it always there? Does it go away if you work harder?

If I’m working on something and I feel like I did a good job, it goes away for a little while. If I write a new chunk of material I love, it goes away for a little bit. If I feel like I have a lot of shows with new material, it goes away for a bit. Then there’s all the other unrelated-to-comedy shit—the therapy, trying to feel like I’m OK where I am.

What effect does it have on you? Does it give you some fire in a way that helps you?

It definitely drives me. That at least is good. The desire to feel like you’re not a loser drives me. I don’t know if that’s the healthiest thing—to be motivated by a fear of hating yourself. But it definitely helps. In a perfect world I would overcome the sense that I suck constantly.

If you did overcome that feeling could you still do comedy?

I used to think maybe not. But I think I have to. For a while I thought dwelling in that darkness and that self-hatred worked, but eventually it becomes more crippling than good. I could definitely still be funny. Some people do better when they’re in a bitter, angry place. I don’t. I think I’m funniest when I’m feeling more optimistic, hopeful about everything.

What about mistakes?

Emotionally I dwell on things forever. I’m an obsessive thinker. I obsess on things I’ve done wrong. Even worse than mistakes, I’ll dwell on what I’m not doing at the moment and what my limitations are.

Give me an example.

What I’m not doing is writing more. Each day that goes by, I think, “I meant to write, but I didn’t.” And the days go by.

Rather than sitting at the computer and writing, actually finishing things and fleshing out thoughts, I just rely on going on stage and dicking around until the funny parts occur to me. I’m constantly tormented by the fact that if I could get organized enough to just sit down and write, I would be 50 times further than I am today, creatively.

Professionally, there are a million things I could do. I’m always asked if I have any ideas for sitcoms or dramas or anything I’d like to pitch. I have a lot of opportunities to come in and have meetings with people who can make decisions on these things… and I don’t.

I’ve had people over the years approach me and say, “Come in any time with movie ideas!” These are people who could make these things happen. I get excited about it, I think about it, I come up with a few ideas, and then I get all fucking ADD and the opportunity slips away. Maybe I should have eaten some protein before we had this conversation. I could have been more upbeat.

What advice would you give to yourself from the outside—or to someone in a similar situation?

On days when I’m feeling positive, I say, “Look. Wait a second. I started doing standup just 17 years ago, just for the hell of it really, and I thought ‘I’ll do this until I figure out what I can really earn a living doing.’ And now all of a sudden I’m really proud of what I can do with standup comedy, I’m a much better standup comic than I ever imagined I would be, and I’ve made a decent living doing it. And it seems like I’m poised to do better.” I’m living the life I’ve always wanted, in a lot of ways. I try to be as appreciative of what I’ve been given as possible. When I’m feeling upbeat that helps.

Staying grateful and even sometimes being so fucking corny as making a mental list of what I have to be grateful for. That definitely helps, when I’m feeling positive. I don’t know if it’s the chicken or egg. When I’m feeling in a darker place, my perception is that everything sucks and even though I’ve done this, it seems I should have done more. Trying to stay grateful helps.

And a lot of times, I’ll think, “I’m not really that talented, and I have maximized what I’ve gotten.” And that I should stop kicking the shit out of myself.

“Who the fuck am I to think I was entitled to this great career? That I should have done more? That I deserved more?”

It’s a paradoxical way to look at it—positive and negative at the same time. Who the fuck am I to think I was entitled to this great career? That I should have done more? That I deserved more? I’ve done more than I deserved. Things are going fine.

It’s easy to dwell on how I fucked things up with myself and others, but really, given where I thought this was going to end up when I started, I’m pretty happy with how it’s played out.

But you are successful. So is it that you just think you should be more successful? Or that somehow you’re a fraud because you don’t work that hard and you’ve achieved this success?

You’re coming up with angles that are true that I haven’t thought of!

I’m just wondering what it’s like for you.

A lot of it is fear of the future. Do I want to be a 55-year-old man, working the clubs, traveling around the country, not doing theaters, not being enough of a name? If I didn’t have this family to support, if I wasn’t living in the city, if we weren’t in the greatest fucking economic downturn ever, I would probably feel I was fine.

Yes, I feel, not like a fraud, but frustrated with myself and my limitations. They don’t feel like they’re creative limitations. I just get too distracted by life and don’t focus on what matters to me.

What question should I have asked you that I didn’t ask?

How I feel about Jesus? Gay porn, yea or nay?

As I talk to you, some things are crystallizing in my head. It’s actually very helpful. I hadn’t thought about it this way. Trying to focus on what really it is that matters to me.

When I start to feel like a failure, I realize, it’s really that I haven’t worked harder on my standup. And I can do that. Focusing on things that are manageable, that can be done, things I have control over. Right now I’m feeling like shit. I have two shows tonight. Now’s the time, I’ll definitely crank out some new shit before then. And that gives me a sense of optimism and hope I’m not being crushed by this broader system.

What is it that distracts you?

It’s a lot of things. I have three kids, and I love them more than anything. It’s easy to obsess, not even in a healthy way, distracted by worries about them and their future and how they’re doing. How they feel and how they’re coping. Thoughts that are not productive.

“For years on the road I’d finish the shows and stay out all night and get in all sorts of trouble—trying to escape that fear by ripping it up out there.”

When I’m actually with them, doing things with them, I feel great, fueled by that. But it’s so easy to wallow in self-hatred, like, “Shit, I fucked up. I let my relationship fall apart. Now they’re living with their mom and I don’t see them.” Instead of letting that fuel me creatively, it becomes a sinkhole.

Other things are just general bullshit. I’m easily distracted—I start watching television. I start searching the Web.
For years I’d go on the road and I’d finish the shows and instead of going back to the hotel room and reading, I’d stay out all night and get in all sorts of trouble—trying to escape that sense of fear by ripping it up out there. Getting done with the shows and riding that high, thinking, “I am good, and what better way to keep that going than partying?” That’s been an enormous distraction from my work.

You mentioned letting worry about your kids fuel you creatively versus getting caught in a sinkhole. What’s the trick to letting it fuel you creatively? How do you direct that negative energy to something positive?

I’ve tried to on occasion just write about it and feel being fueled by it creatively is very difficult. Standup in particular is a very specific thing. There’s things you want to talk about, to express—but you have to be funny. And you have to funny to a mass audience. It’s a constant frustrating thing. I might write something I think resonates with me and would with other people in my situation, but it just doesn’t get the laughs you need because you’re performing it for 20-year-olds in the Comedy Cellar.

There’s enormous frustration there. The way it has fueled me recently is this sense that I want my kids to be proud of me, and if I’m not good at what I do, and if I’m not trying my hardest at what I do, then all this shit I’m putting them through because of my demons has been a waste. The very least I can do for them is to be the best I can. That does help me feel like, “OK, take your shit more seriously. Don’t just throw away stage time. Don’t let the days go by without having done any work.” That’s been working. Then sometimes I feel what they need from me is to be relatively content and to be there for them, so I can’t torture myself over this stuff. But I do anyway.

Do you think part of it is that you blame yourself for things that are out of your control?

It could be. I tend to blame myself for everything. There’s an expression I’ve heard used for people in my shoes, people who see themselves like I see myself. I feel like I’m “the piece of shit at the center of the universe.” It’s a paradox. You feel like you’re so shitty you ruin everything, but you’re so important and powerful that you caused it, that you actually are to blame for everything. I’m doing the best I can, and maybe that’s enough. It depends on how much sugar I’ve had that day.