OVERTHINKING The Increasing Relevance Of Conan O'Brien

A.K.A. Conan, The Boomer Millennial

Welcome to a semi-regular

Letters From African America

segment called OVERTHINKING — where I’ll not only overthink a singular topic, but also construct a paranoid conspiracy theory about it.

Two things that are weirdly important to me are coming to a head tonight: The 97th Academy Awards and the 61-year-oldConan O’Brien. This occurrence, rarer than the recent alignment of planets in our solar system, makes this the perfect moment to over-think the increasing relevance of one of America’s finest late-night hosts.

To understand my personal connection with the Oscars and Conan, we must first travel back to my youth as a sheltered Black kid in South-Central Los Angeles who loved the movies and was obsessed with television. Growing up blocks away from USC, for instance, made for a specific kind of magic when I learned that its creator honed his skills in my neck of the woods.

We also lived close to the Shrine Auditorium, the former home of The Academy Awards before they switched to the Kodak Theater in 2002. Every year, traffic jams connected to the Oscars would make our journeys home from school or wherever else tediously slow for a few days. But there was a magic in that as well. The entire city was abuzz with labor and interest in this crazy thing called movies. And it was kind of cool knowing that I was a part of this interconnected entertainment hive.

My family was deeply engrained in the neighborhood. So much so, that once, my dad walked me up to a group of old friends hanging out in a park and on the way back to car said “Hey, you know that one guy we just met?… He was one of the guys who stole those Oscars.”

In L.A., everything is connected. And my parents, knowing how interested I was in becoming a filmmaker, allowed me to stay up during the awards, often tending to their own interests as I did. There I was, a kid with his bowl of popcorn, a box of Red Vines, and the greatest soda known to mankind: Cactus Cooler — watching an event I dreamed of someday being a part of, which was happening live, one mile away.

I had a similar buzz somewhere in middle school when I graduated to having a TV in my bedroom and discovered a strange show with a tall man who seemed to be trapped on a stage during his monologue, resulting in odd behavior like pretending his hair was a shark. There was no need to flip the channel because his style of humor flipped them for you. Long before I had the thought of pursuing a life in comedy, I knew that the energy surrounding Late Night with Conan O’Brien was one worth chasing.

But why is it, exactly, that Conan still has wide appeal, as evidenced by his viral 2024 appearance on Hot Ones to promote his HBO travel series:

Well, I have a theory about that, and late night as a whole, so join me as we go down the rabbit hole…

WHAT CONAN REPRESENTS (A.K.A. CONAN, THE BOOMER MILLENNIAL)

No one but Conan, in the wide history of white entertainment, has had such a public millennial experience. America watched as he learned the lesson all millennials like myself have, before many of us even had to: The old ways are dead, and your emotional ties to them will hurt you.

He is, after all, the man who lost The Tonight Show because of an older man who refused to retire and his own refusal to let the show air past its historic time slot of 11:30pm.

He had no idea that time slots would soon go the way of the dinosaur.

But what he did after that was sort of miraculous, and I would argue, the same thing millennials and Gen Z have adopted in the fractured media landscape.