Could Have Been Cuter

By the end of sophomore year of high school, I am not only fully obsessed with all things Conan, I have also established regular afternoon watch parties of my favorite Late Night sketches. The summer before junior year, my mom and I drive my brother back to college in Boston, and I have only one request: I want to go to Brookline.

Brookline, Massachusetts is the town where Conan grew up in his large family with 5 other kids and intimidatingly smart and successful parents - a doctor (he’s a microbiologist) and a lawyer (one of the first women in that field). My mom, ever supportive, agrees to take me to Brookline. After we move my brother into his apartment, out of the city we go on a pilgrimage that was sacred, but only to me.

We visit the town. We visit the library, the Catholic Church, and Brookline High School. I go inside like I own the place and visit the book store. I get a lot of weird looks. I buy a notebook, a pen, and a t-shirt. I still have all three. I get some weird looks, but who would begrudge a high school kid some high school stuff? I have come across one Brookline address on the internet that I don’t ask to visit. The house.

During a later visit, my brother and his girlfriend drive me past Conan’s childhood home. The one where his parents still live. I get there and feel an almost immediate shame. This is someone’s home. I have no business being here. People on the internet have no shame, but I do. I get out of the car and walk down the block, taking in the trees that line the road and glance up at the house. Hello, house. Nice to meet you. Years later I would hear that not only does Ruth O’Brien love it when people confess that they love Conan, she spent the early Late Night years handing out keychains as tokens of appreciation. I don’t want to impose to get one of those.

Summer turns to fall, and my mom asks me an important question: what do you want to do for your 16th birthday? I have one and only one answer: I want to go to New York to see Conan, and I want to take my three best friends.

I am surprised and delighted when Alex, Vanessa, and Lisa’s parents say they can come to New York. I am lighter than air in my tie dye when I dial the NBC ticket office (3056) and request my birthday tickets. The gut punch comes when the NBC page that answers the phone (again, can I have this job?) be tells me that tickets for my birthday are open, but the day I need, the next day, is full. The day I need is Friday, November 17. I can’t leave school early enough to get there for my Thursday birthday, and my friends and I can’t take off of school. I cant see Conan for my birthday. I’m crushed.

“Have you ever heard of the Upright Citizens Brigade theater?” He asks.

“I saw them once on Conan. They have a theater?” I ask.

“Yep. It’s in Chelsea. 23rd and 6th ave. No show over $5. You should call them.” He says, and I never get his name. I never ask for it. He offers this information to a disappointed comedy girl. He has no idea how important this is, or how much it would come to mean.

For my 16th birthday, my mom takes me, Vanessa, Alex, and Lisa to New York. On the car ride there, we listen to Rasputin by Abba on constant repeat. We memorize the words and choreograph a dance. We get to the city, and check into the hotel. We float down the street to Rockefeller Center. After the tour (where I am shushed for being an NBC know-it-all), we ride along as Conan drives the desk at the NBC experience. We buy the tape. “See you at our wedding!” I say as digital Conan waves goodbye.

Since Conan is off the table, we go to the UCB theatre. We stumble into a little space that used to be solely used for porn. And we watch comedy. We miss the 8pm time slot because of dinner (at a restaurant called HASTA LA PASTA in the village because I think that is hilarious). We make it for the 10pm show on Friday, November 17, 2000. The Swarm. I have been 16 for one day.

The Swarm is 6 people: 5 men and one woman. And I recognize almost all of them from sketches. From Conan sketches. One shaggy blond dude with glasses seems extra familiar - my brain echoes “ICED TEA TWO THOUSAND!” From a sketch about things being fancier because of the year 2000. Another guy looks remarkably similar to Spock from a Conan and Andy staring contest. But it can’t be. Can it? My face hurts from smiling and my comedy heart is racing.

That was the beginning of UCB for me.

During the weekend, we visit FAO Schwartz and take a picture with a boy dressed like a toy soldier. We pretend to smooch a wooden sandwich board of David Letterman. We don’t actually smooch it because it’s covered in pigeon shit and we are from the suburbs.

We have the most amazing days, nights, and experiences. The day we leave, Sunday, we see a matinee of Annie, Get Your Gun. “Could have been cuter,” Vanessa famously says after someone declared the show to be cute. My mom takes a comedic stumble in the street, but is ok. It becomes a joke for the rest of our lives. Despite this, I constantly thank her. She sleeps on the hotel room floor so that my friends and I can have the beds, and she never bats an eye of complaint, even when we try to get her to sleep in a bed. I am the luckiest kid. Person. Human.

On the way home, we stop at Maryland House on 95 and take a picture with Bob’s Big Boy for no other reason than that is what Conan’s hair resembles. His words, not mine.

Now I am 16. I know who I am, but what will I do with this knowledge? With this personality? How will I conquer this angst?

This was still the beginning. But there’s so, so much more.