long story short

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.

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.

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. 

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. 

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. 

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. 

Back in the "old normal," driving through the hellish Metro Manila traffic required a certain level of calmness, which on most days (and nights) for me meant listening to podcasts. It started out as a nostalgia thing - I wanted to relive my college years by listening to late-2000s The Morning Rush episodes (with just Chico and Delamar). But after the novelty of that wore off, I eventually stumbled upon content that  resonated more with my current interests: podcasts with my favorite comedians and screenwriters.

Marc Maron is the complete opposite of that. He connects with the audience, both through his stand-ups and his podcast, by revealing his soul, his innermost thoughts. Unlike Jerry, much of his comedy is shaped by his most seminal experiences. His life goes hand-in-hand with the art he produces. Much of his work is shaped by pain and grief. The way he performs is always in relation to his current state of mind. And that's what makes his comedy so resonant, because he doesn't shy away from what is messy and scary and f*cked up about his life, and life in general. 

Marc notes that Jerry's kind of comedy isn't much of a risk, as it doesn't involve putting himself in his comedy. But for Jerry, the very act of delivering jokes is putting himself out there. He doesn't have to go into the whys and hows of what makes his comedy work and why he enjoys doing it. Unlike Marc, he doesn't derive pleasure from figuring out certain aspects of himself through his work. He just wants to write jokes, period.

I loved that despite their very opposing views, they were actually hilarious together. It was like listening to two philosophers having different beliefs on what it means to be good. While their comedic ideologies are at odds with each other, no one is entirely right or wrong. The conversation brought out such unique insights on comedy and what it can mean to us. Marc tries to understand Jerry's way of thinking, because he wants to find out who the real "Jerry" behind the jokes is. But this is the real Jerry: the one that writes jokes. His comedy is as simple and straightforward as he is. On the other hand, Marc's comedic persona is complex and raw and transparent. He doesn't rely on what he wrote on paper - he tries out what he feels on the spot, he engages with his audience, he wears his heart on his sleeve. They're both honest about their craft, in their own ways. But they have a different way of expressing that. 

This is crucial for me, because it got me thinking about what comedy means to me. What attracts me to it and what makes it speak to me. Growing up, it was probably really just for the laughs. But eventually, many experiences - both traumatic and triumphant - changed the lens through which I saw life. I found comedy to be comforting, because it wasn't afraid to hit all kinds of buttons at the same time, to get a reaction out of you. Marc said it best: comedy had a way of putting the darkest parts of life into little packages that made you laugh, sure, ans it also put things into an interesting perspective.

It can be a way to deflect. But the thing about really great jokes? It deflects, and then almost immediately, it boomerangs right back at you. Shoot, recoil. And then finally, a moment of realization. And all in just a few seconds.

I agree that comedy doesn't have to come from a broken place, nor does it have to bring you there. But I think I'm partial to Marc's point of view. Personally, I prefer comedy when it comes from a place of pain and healing; when it finds wisdom in the difficult aspects of life. Because that's the kind of comedy that got me out of some of my darkest days. (Looking at you, Fleabag and BoJack Horseman.) And it's the kind of comedy that has the potential to actually change things, to shake up the status quo. I have full respect for Jerry and Seinfeld - that whole school of "comedy about nothing" - because, yes it succeeds brilliantly at what it attempts to do, and it doesn't require you to wrestle with difficult questions to enjoy it. We need that kind of funny.

But especially in these times, comedy has to mean something. It has to make sense of it all, and attempt to move people into action. Otherwise, how can we elevate the discourse? Why waste that opportunity to do so, right? Comedy is relatable. So why not make it matter at every chance?

That's the kind of writing that feels more transcendental to me. When the writing results in laughter and tears and reflection.

"An essential element in comedy: rage. Aggression, confrontation, resentment, irritation - there are varieties of it. You can't not have it. If you don't have it, you're not gonna get laughs. But I think the greatest use of it, of that rage, is to process it through a laugh machine."

There will always be things to laugh about. And we will always find the need for things to make us laugh, even and especially as we process grief, joy, fear, all kinds of emotions. I guess it's up to us - the audience - to decide whether we need the why behind what makes us laugh. Personally, I like coming face-to-face with the different spectrums of anger and sadness that compels me to find hilarity in the ridiculousness of life. It's challenging and rewarding. And it's oddly comforting.

There is something about comedy that sees you. At least, that's how it feels like to me. Sometimes, there are laughs that make us ask ourselves truly difficult questions. At the end of the day, if it gives us a clearer picture of who we are, and it allows us to keep going, then the joke has outlived its punch line and has done something truly meaningful. That's where the power of comedy lies. Not just in the immediate laugh, but in the lingering chuckle - and sentiment - that it leaves us with. 

And that's why I'm Team Marc on this one. But I'm still giving points to Jerry for Comedians in Cars Getting Coffee, at least. 

When I was a teenager, one of the biggest perks of finally sleeping in my own room was getting to stay up late. Back then, getting lost in the peculiar algorithms of YouTube was not a thing yet. Instead, what excited me the most was getting to catch all these "adult" shows on cable which, at the time, were beginning to be understandable to me. Adult Swim, Sex and the City, and yes, the three late night shows: Late Show with David Letterman, The Tonight Show with Jay Leno, and Late Night with Conan O'Brien.

Late night shows were a particularly endearing breed for me. It had celebrity interviews, sure, but the real draw was the personality behind the table. I've always taken these shows at face value and liked them for the different flavors each one gave. Dave, for his sardonic, cynical humor especially in his Top Ten. Jay, for his rapid-fire monologue and Headlines. And Conan. Oh Conan. I learned the words "shenanigans," "moral outrage," and "noches de pasion" because of Late Night. I had the softest spot for him even when he was the one that most confounded me. He was too quick, too sharp for fifteen-year-old me, but it was always a delight trying to catch up with him and be in on the ride.

When the whole Tonight Show controversy erupted in 2010, I followed it obsessively online. At the time, none of my other friends watched these shows, so it felt like this devastating blow that I couldn't share with anyone. I liked Jay, sure, but the whole shake up was not a good look on him at all. It only solidified what I've always felt through the years: Team Conan all the way. He wasn't given enough leeway with his version of the Tonight Show. And it was so unfair.

After that, the late night scene was no longer the same. Since then, new players have come into the fray. Fallon, Meyers, Corden, Colbert, Kimmel, Noah - these guys are now holding the fort. But the format has changed in so many ways - and necessarily so, given the changes in technology and the way audiences consume media. They now have more sketches and gimmicks, and rely on the virality of each individual segment rather than the cohesiveness of one whole show. Which isn't entirely bad, per se. I do like their content too. It's just different.

Which, I guess, is why I felt the need to read this book when I got an epub copy. I wanted to know what really went behind the scenes, what changed the network's mind, and at what point NBC realized that the late night landscape was going to be significantly shaken again. (Incidentally, I was also really curious to know how the contracts were drafted in the negotiations.)

It's quite ironic that all this went down precisely because they were trying to avoid the exact same thing that happened between David Letterman and Jay Leno back in the 1990s, following Johnny Carson's retirement from The Tonight Show. In the early 2000s, NBC wanted to have a "Prince of Wales" succession clause to secure the person who will "inherit" the throne of The Tonight Show and avoid any drama. The idea was brilliant and the identity of who the successor will be was clear: Conan. What did them all in was the timing.

I'll save you the trouble of reading the book and just refer you to the Wikipedia page linked above if you want to know the timeline of how it all went. But more than just the narration of events, what stood out more in the The War for Late Night was the very personal, and authentic depiction of the actual people involved in the fray. The network executives, the agents, the producers, even the competition at the time. (There's a great chapter on Letterman, but also a recognition of the other key players like Kimmel, Fallon, Colbert, and Stewart.) Most importantly, Conan and Jay.

I've always been Team Conan. He's loved by all, from young intellectuals to fellow comedians and artists. I love the guy, I admire the guy, I binge-consume any content of his that I can get my hands on (Podcast? check; Late Night classics? check; interviews on YouTube? check; Conan without Borders? check.) And the book is actually very sympathetic towards him, showing that in many ways, he really was the victim here. Many other factors were at play: the timing, the ratings, the lead-in, the bind that NBC head Gaspin was in considering the network's descent from the ranks. But it still all boils down to the fact that NBC didn't want him enough. They didn't want him to go elsewhere, but they were willing to break a promise made to him just to make more money. He didn't deserve to have The Tonight Show taken away from him like that.

But, the book also did a good job of showing Jay's side. He's a no nonsense kind of comedian. He wasn't innovative, he wasn't a genius. He didn't go to Harvard like Conan. But - and this is crucial - people loved him. He didn't appeal to the intellectuals, sure, but he is certainly well-liked by even the simplest of folks in Nebraska. He had mass appeal. And to top that off, he worked hard. Really hard. He didn't play into the celebrity schtick, he didn't mind not winning awards. He ran The Tonight Show like a ship, and it always landed at the same place: the top. He consistently beat Letterman in the ratings, something Conan couldn't do. You can't fault the network for wanting to give the keys back to him, especially after the variety show they offered him did not work.

Conan got a shitty lead-in during his stint at The Tonight Show because the network botched it with The Jay Leno show at 10:00 pm. But the fault here is to be placed squarely on the lawyers. Jay had the leverage between the two of them because his lawyers were able to secure for him a "pay-and-play" contract, as opposed to the usual "pay-or-play" (which was what Conan had). This contract guaranteed NBC would both air his program and pay him for up to two years, whether the program continued or not. This is completely different from Conan's The Tonight Show contract, which provided that NBC can either play his program for two years or pull the plug on the show and just pay him off, by network prerogative. Comparing both, NBC stood to lose more if they broke the contract with Jay than with Conan. The pay-and-play was unusual in the TV setting at the time, and there was no way Conan's lawyers could have anticipated that that was possible, because it wasn't an industry standard. But Jay's lawyers did. So his ass was saved by the network instead.

The book was published in 2010. Reading it now, in 2020, it's easy to say that Conan still eventually got the better end of the deal in the long run. Sure he never got to fully enjoy his tenure as the host of The Tonight Show. But he was able to diversify his content: he got to set up his own production company, has a podcast, shoots for a Netflix docuseries, has mockumentary shorts involving his staff, and still has a late night talk show, albeit on a cable channel now. He has the freedom to do whatever he wants, and that has only resulted in more hilarious, genre-bending, and entertaining content since then. In particular, his podcast and travel series show a different side of him, one that allows him to flesh out his conversations with his interviewee because he has more time to breathe and just be. The interviews he does now no longer focus on just, say, promoting a movie, or rehashing an oft-repeated anecdote. He has the opportunity to really get to know them, find out their stories, and all while sharing a little part of himself. Even in other forms of media, he's still somehow changing the game.

But at the same time, I can't help but wonder - what could have been? If he had remained at The Tonight Show, I think he would have eventually veered towards the same content (aimed at virality), while still maintaining his identity. Breaking the norms, making people uncomfortable, finding the silver lining even at the perverse. He may not be doing a Lipsync Battle or Carpool Karaoke - but I think audiences would have loved an updated Triumph the Insult Comic Dog just the same. He could have been breaking even more barriers, given the timeslot's reach.

Alas, it wasn't meant to be. And as with most things, we have no other choice but to look at it as a glass-half-full kind of situation. The late night format as we knew it had to end somehow. It was just unfortunate that it had to claim one of the greats as its victim.

One of my favorite post-Tonight Show Conan content though, is his speech for the 2010 graduating class of Dartmouth. It has all the ingredients of everything Conan: hilarious, ridiculous, well-researched, self-deprecating, and full of wit. But what stood out about this speech - and what makes me re-watch it from time to time - is his honesty. And the ability to turn his heartbreak into a catalyst for something more meaningful.

It's definitely a beautiful way of looking at failure. The road to success will always be paved with disappointments. That's a fact of life that we all have to come to terms with. But real success isn't solely measured by your ability to reach the top. It's also about the kind of person you've become while you were at it. Did you take advantage of someone else? Did you steal? Did you cause pain? I guess, my biggest take away from this book is that when things like this happen, there are no clear winners. On paper, there might be. But victory lies with whoever walked away with grace, humility, and compassion. So, with every triumph, we must never forget to ask: "At what cost?"

Forever echoing my favorite sign off from Conan: