A Comedy Masterclass in Podcasts: Part 2

Conan O'Brien Needs A Friend, Episode 13: Stephen Colbert
Conan O'Brien Needs A Friend, Episode 13: Stephen Colbert


I've been meaning to write about this episode since the first time I heard it in 2019. And I've attempted to do so in the many times I've gone back to it since then. It's a fantastic episode, not just of "Conan O'Brien Needs A Friend," but podcasting in general. Conversations like these are what make this format so fulfilling. Podcasts allow the host and the guest to truly immerse themselves in a topic without the expectation of immediate audience reactions or without much worry over time. But also, the entire hour of this show was a great distillation of what I love most about comedy. A lot of people dismiss the genre as "light." Frivolous. Not serious. But there is a great deal of depth and poignancy behind why it feels light. And it often takes a tremendous amount of sheer will - one that has overtaken or continues to overtake suffering - to create something that triggers release: laughter. With genuine laughter comes levity, and with levity comes ease. This episode demonstrates clearly why and how comedy heals.

(It's also a great introspection on Catholicism, and how our faith compels us to view suffering as imperative to redemption. Who would've thought, huh? On a comedy podcast!)

Let's start in media res: Conan opened up about growing up and suffering from anxiety. Shortly after, Stephen began talking about the tragedy of losing his dad and his two brothers on a plane crash when he was 10 years old. They were en route to the Canterbury School, a boarding school in Connecticut, when the plane was trying to land. It changed his family's life instantly, and shattered him completely. 

Eventually, the two comedians found common ground on how comedy really, truly saved their lives. Comedy, for them, came from this sudden, unexplainable compulsion to enter a plane of "magical thinking." It was relying so much on your imagination, of being so deep in a process of self-reflection, in order to channel something new. For Stephen, it was entering this realm of possibilities inside of head, of trying to change how things were and finding meaning to reality.

Stephen: "I had a magical thinking about suffering and about forbearance and patience. Patience and forbearance of suffering. It would require enormous magic for that not to have happened [to my dad and brothers]. But what kind of brother or son would I be if I didn't at least attempt the magic?" 

With that "magical thinking" also came the acceptance of suffering; in fact, even thinking that pain was necessary in order to achieve some kind of meaning. The logic is that somehow, getting to the realm of "magical thinking" offsets the guilt of being alive or the guilt of having good fortune.

Conan: "I grew up an anxious person, very anxious person, and struggled with anxiety, and I really thought in a Catholic way that everything anything good had to come through suffering. I really believe that you have to be miserable."

Both these guys were raised in a very intellectual Catholic household. Both their dads were medical doctors (Stephen's dad was the dean of Yale Medical School; Conan's dad was a professor at Harvard Medical School). Conan's mom was a lawyer from Yale. They came from a large family (Stephen had 10 older siblings; Conan was the 4th of 6 children). But more than that, they were kindred spirits in how they both constructed a belief system that misery was required for anything good to happen. 

There was a beautiful discussion of how this was necessarily tied to their faith. 

Stephen: "I'm a Roman Catholic, and an 11-year-old altar boy. Very devout household. And the image of Christ on the cross - the highest aspiration is to be able to take up your cross and to alchemize suffering into gold. But you can't have gold without suffering. To the point where I had a magical thinking."

I have gone almost three decades of my life without anyone else understanding this undercurrent of unexplainable sadness I carry with me, a sadness so baffling considering I am often the most cheerful and most optimistic in almost all of my circles. It wasn't until this podcast that I realized I wasn't alone. I have lived a very privileged life. In many ways, I have been shielded from harsh difficulties because of circumstances outside my control. (Class, mostly.) It has always made me feel a kind of much-deserved guilt, that I don't deserve to have these things. And yet, I do have a unique collection of heartaches. The death of numerous family members since I was 13; parents who only tolerate each other; an operation that permanently severed certain body parts - these all change the equation. To reconcile my privilege and my many griefs, my mind learned to cope by creating this twisted way of looking at the world. Anguish was necessary to counterpoise my good fortune, I'd think to myself. But the continuous luck - the "rewards" I got after going through those sufferings - would just add more to my shame and sadness. "At what cost? My loved ones' lives? I don't deserve any good fortune that came out of overcoming that grief." And so begins an endless cycle of gloom and guilt.

At which point, the "magical thinking" comes in. The magical thinking that maybe I could turn back time. Or that maybe, I can create my own reality. The former is impossible; I just settle with leaving the what ifs in my imagination. As for the latter, it's the part where I intentionally disassociate from this self-defeating cycle, and just decide to power through. That conscious conquering - I get that by making jokes, trying to make people laugh. By putting a bubbly, fun, overly optimistic facade. The "magic" happens when I actually start to believe it. When it doesn't feel fake. When it starts to touch that part of me that floats through the undertow of sadness. And for a moment, the gears of the endless cycle screech to a halt. "I am capable of making people happy without putting them through misery. I can do that for others. Maybe I can do that to myself, too." And if I want it bad enough, if I think hard enough, that magic will erase my woes and work on me too. 

Conan: "I felt like I suffered through other things, and they felt very powerful to me. And I engaged in magical thinking and put myself through a lot of torture. And here’s the crazy thing what happens when you do that, and then magical things start to happen for you."

It's no coincidence that this intersects with my favorite book by Joan Didion, "The Year of Magical Thinking." It is a masterful account of Joan's denial and acceptance over her husband's death. In exquisite, melancholic, almost poetic detail, she invites us into the head space of an unexpected widow, who was at the same time taking care of a 39-year-old daughter in a coma. Here, she explores her inner voice doing the "magical thinking" -  her way of pervading through her suffering was to freeze her grief, as if preserving it in amber. Charging his phone, putting his shoes by the door. One can say it was denial, but many modern sociologists also argue that it's the self's way of manifesting: of giving power to her thoughts like a child, "as if her thoughts or wishes had the power to reverse the narrative, change the outcome." Studies show that any form of "magical thinking" - a belief system that your thoughts can have an influence in the course of events in real life - as adaptive and healing. It can reinforce a suffering person's sense of stability and control. It's advanced-level denial.  

It's not an easy thing to explain, justify, or even rationalize. But I'm so glad Conan and Stephen were able to allow themselves enough vulnerability in that episode that they were able to bring about this truth. To recognize that this coping mechanism isn't unique to each of them. And that this salves the wounds of others too. This suffering, this guilt, this agony - what was it for? What was I supposed to do with it and what was it supposed to do with me?

We embrace the "magical thinking" because we want to justify that suffering is just the prerequisite for any kind of metaphorical or literal reward. A transactional way of looking at life - a lot of therapists will say it's not healthy. But powering through - it happens. And when it does, it just perpetuates itself. It is able to manifest a new reality. 

"The magical thinking magically thinks that the magical thinking worked."

At many points in my life, I feel like it is my faith that consistently pulls me out from a dark place. But - to an embarrassing degree - I place my reverence of the power of laughter on the same pedestal. I am able to access that magical plane because I try to find the hilarity in the saddest, most absurd, most painful situations in my life. I have suffered so badly that I could only end up laughing about it. I carry so much unexplainable sadness that I have no choice but to make fun of it. That's the real triumph, the redemptive coup de grace against that suffering. Losing a loved one, losing a part of your reproductive organs; been there, done that. And when I am truly able to "make light" of it - when I start to believe it and the magic happens - it keeps me moving.

This post is hardly a good distillation of that podcast, nor is it a clear explanation of what that mindset is and how it works. But I just... got it. I was shocked at how much I did. I was stunned at how much they accurately described this affliction. It was so familiar. And it was so powerful. And every time I feel lost or burdened, I find myself coming back to this episode. There will always be suffering. And maybe at the end of the suffering will always be a reward. Maybe we won't always deserve it. But - and I sure hope so - there will always be room for laughter, and there will always be space for magic. 


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