How I Connected With My Teen Through Comedy, Music, and Desperation

I recently watched a Netflix comedy special that came out five years ago because I have a teenage son and I am desperate for connection.

That probably makes things sound a little more dire than they actually are, but hey, this is the internet, and I have to do something bold to capture your attention or risk losing your interest, and thus, losing my reason for existing.

Haha. Very Bo Burnham-coded, right?

Anyway, yes, Bo Burnham’s Inside was the Netflix comedy special. I watched it now, in the year 2026, for one reason only: my oldest child, who is about to turn fifteen and just started high school, has mentioned on several occasions that he enjoyed it.

I’m pretty close with my kids. That’s probably obvious considering it’s what I’ve been writing about for over a decade now. However, as these things tend to go, the tether connecting us, which once felt like a metal chain you might see on an unpredictable pit bull, feels more and more like a fraying strand of yarn.

Kids get older. Their lives no longer revolve around you. The untethering somehow happens both slowly and rapidly. Like the tortoise and the hare combined powers. One day you look up from your phone (you now spend an inordinate amount of time checking your teenager’s location even when he’s always at the same place—school) and think, “Wow, he’s been gone for like 14 hours doing school and band and somehow band again?” Those long-ago days when you used to sit on the couch together watching Jake and the Neverland Pirates and Sofia the First for hours at a time feel like a fever dream.

So, when they mention something they like, even in passing, you latch on, much like they used to cling to your leg on the first day of pre-school.

My wife was out of town at a friend’s wedding. My daughter was at a birthday party. The dogs were occupied trying to eat each other. The boys and I weren’t doing much of anything, so I casually told my oldest I was going to give that Bo Burnham show a try (wink-wink). He flopped down on the couch and told his younger brother to get out because the content was inappropriate for his age.

(I had already checked the content ratings online because I’m a good parent. I’m not super concerned about what my older kids watch, but I know it can be embarrassing for kids when certain topics come up with your parents in the room. I felt like we were mostly in the clear.)

Other than checking for potentially offensive content, I came in completely blind to the special; I had no idea who Bo Burnham was other than Phoebe Bridgers’ somewhat-secret-but-not-so-secret-anymore boyfriend. I’m a bit of a Phoebe Bridgers guy, so I had made a few sorties recently, attempting to forge a connection with my son over our shared interests.

My interest: music by Phoebe Bridgers.

His interest (apparently?): comedy by Bo Burnham.

“Hey, your guy has a writing credit on Phoebe Bridgers’ new single!” I announced one evening, peering expectantly at my son as he sat staring at his computer, one ear covered with his headphones, the other ear uncovered.

“Who is my guy?” he asked, eyes not straying from the computer screen.

“Bo Burnham.”

“Oh.”

“The song is called ‘Lost Boys.’ Apparently, he helped write it! Guess we know what he’s been doing lately.”

“Ok.”

And then a few weeks later.

“Hey, your guy does vocals on the first track of Phoebe Bridgers’ new album!”

“Who?”

“Bo Burnham!”

“Oh, ok.”

Things were going well. It was clearly time to take things to the next level with Operation Meet My Son Where He Was (at some point in the not-too-distant past).

I quickly learned that Bo Burnham does a lot of musical comedy (who knew?), so it makes a lot of sense now that he could seamlessly transition into working with Phoebe Bridgers on her music. Before watching his special, I was a bit confused. It was unclear to me how joke writing and writing sad song lyrics would pair.

Inside was filmed during COVID, and the unique aspect is that Burnham shot and edited the entire thing by himself over the course of a year in his guesthouse. He goes from clean-shaven with short hair to unkempt and shaggy as the special progresses to drive home the theme of isolation.

The special is a series of musical numbers, sketches, and stylized self-interview moments. I enjoyed it both because it was funny and creative, and because it focused on a lot of the angsty things I struggle with, like feelings of hopelessness while living in a deteriorating world and the seeming pointlessness of doing art or comedy or writing when people everywhere are suffering. (Like, why am I even writing this? Nobody knows. Everyone is dying, and natural disasters are increasing at an alarming pace. Do something with your life, Andrew!)

In one of his opening songs, “Comedy,” Burnham sings about how he should try to make a difference (or maybe just shut up for once) before ultimately deciding that, no, that’s no fun; he still wants to do comedy. He still wants to create, to be heard and seen. He satirically concludes that the only path forward is to heal the world with comedy.

If you wake up in a house that's full of smoke/Don't panic/Call me, and I'll tell you a joke

Obviously, this isn’t groundbreaking sentiment—artists lament these persistent feelings and anxieties all the time. That making art isn’t enough when the world is so bad. However, the production and delivery were fun, and at least to me, unique. And it was cool that my son could provide fun background tidbits about which parts of the show were particularly popular and how Burnham achieved certain production effects.

I also liked how Burnham leaned into the apparent hypocrisy of critiquing internet culture while being firmly at the center of that culture (he got his start on YouTube when he was in high school). I’m a big fan of self-awareness. Even if, I suppose, one could argue that self-awareness in this case was mostly being used for the purpose of relatability.

Overall, I thought Inside was great. It’s one of those creations that make you a little angry and depressed because you know you’ll never make anything that good. But hey, I’m mostly glad my son seems to be developing good taste after a rough few years there when it felt like it was going to be all YouTube nonsense all the time forever.

How did the forging a deeper connection over shared interests turn out? Well, let me tell you, things were going pretty well, and then they got dialed up to transcendent.

Towards the end of Inside, Burnham sits down on a stool with a guitar (see the header image above). He says to the camera that he’s not great at playing guitar or singing, but wants to share his song anyway.

When he started playing a song called “That Funny Feeling,” my eyes did the cartoon character surprise thing. I turned to my son. I looked back at the screen. Back at my son.

“What?” he asked.

“I know this song. Phoebe Bridgers sings it!”

I was a helium-filled balloon. I had to tug firmly on my string to stop myself from floating straight up to the ceiling.

We discussed details for a few moments while the song played. I sang along to prove how cool and knowledgeable I was. After a quick internet search, I discovered that the song was written by Burnham, but covered by Bridgers.

“Did you really think with those lyrics that she wrote that song?” my son asked.

Hey, even parents have their blind spots.

Postscript.

A few days later, I picked my son up at school at literally 1:15 a.m. after a Friday night football game that was delayed for several hours by thunderstorms. When you’re in marching band, sometimes you have to put in 18-hour days. That’s how the world works.

“The Outside” by Phoebe Bridgers was playing in the car. I never know if my son notices what music is playing. Or if he cares. I asked him how everything went.

“Fine… It’s kind of funny, you know?”

“What?”

“This song,” he said, tilting his chin toward the console’s screen. “It’s called ‘The Outside,’ and Bo Burnham’s special is called Inside.”

I smiled. Top 5 moment of my life.

“Well, get this,” I said, frantically skipping through the album’s tracks before landing on a song called “Bobby.” “This song is about him!”

“Ok.”

Music to my ears.

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Words by me, Andrew Knott. Best known for duck, Baby-sitters Club, and horse.

My books:

Love’s a Disaster - contemporary fiction about a marriage proposal gone wrong, complicated families, mini-golf, second-chance love, Florida, sword fighting, and punk rock music.

Fatherhood: Dispatches From the Early Years - essays and humor about the very early years of my parenting journey