In May 2009, I had the priv­i­lege of inter­view­ing Greg Giraldo, the dark and bril­liant stand-up come­dian who, sadly, died yes­ter­day at the age of 44. I owe that honor to my friend Joey Gay, who per­suaded the nor­mally reclu­sive Giraldo to speak to me for a series of celebrity inter­views I was doing for Psy­chol­ogy Today.

Giraldo’s intel­li­gence and wit were on dis­play through­out our con­ver­sa­tion, but what struck me most was his depres­sion. “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.” It sad­dened me that some­one so tal­ented could be so hard on him­self. In remem­ber­ing him, part of our task will be to cel­e­brate the remark­able achieve­ments he him­self had dif­fi­culty acknowledging.

In try­ing to fathom Giraldo’s death yes­ter­day from an over­dose of pre­scrip­tion drugs, it’s hard not to look for clues in the things he said when I spoke to him. One answer 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 great come­dian who’s passed away soon after­ward. In 2008, I spoke to George Car­lin just nine days before he died in what turned out to be George Carlin’s last inter­view. Like Car­lin, Greg Giraldo was a genius and an icon­o­clast. He will be missed. —Jay Dixit

The Inter­view

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.

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.

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.

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.