Tessa Greenberg declares: If it’s embarrassing, do it!

Tessa Greenberg is a comedy director, editor, and writer from Brooklyn, NY.

She’s been working in the film and television industry since 2007. She has edited for HBO (How To With John Wilson), directed & written original comedy series on IFC, MTV, and Fuse, and directed commercials for Universal Studios Theme Parks, Fresca, Heinz, Flonase, and LEGO among others.

Tessa honed her comedic filmmaking sensibilities while working for the Upright Citizens Brigade Theatre and their production department, UCB Comedy & Don’t Think Productions where she was a resident director and editor.


What were you like as a teen? (
As a teen, I was a flamboyant theater nerd who was also voted class clown, which honestly is a very high honor! I’d pretend to fall asleep in class and pretend to fall out of my chair for attention, and I’m sure I drove the teachers mad. I thought I wanted to be a Broadway actress, but I only ever got cast in the little weirdo roles which eventually made me realize…I don’t want to fit into anyone else’s mold! I want to make my own mold.
Back then, I knew I was different and weirder than the other kids. Thankfully, I also knew that it was special to be unique. I also had braces for 7 years AND a missing front tooth (with no adult tooth coming in), and I’d put Tic-Tacs and Chiclets in the gap because it made my friends laugh. I was not “hot” in the way boys seemed to like, but I also didn’t try to be and I’m kind of proud of that.
Did you have an un-sexy starter job? 
I was a nanny and barista for many years in my early twenties. I didn’t know any fancy film or production folks and had no ins within the industry, so I eventually took a job making $10/hour as an assistant stage manager at a new sound stage in Brooklyn where I at least had free access to using the studio and equipment. I was in a band at the time, and I’d make these killer, high production value music videos which was a great way to learn the craft of directing and filmmaking.
What do you consider to be your biggest comedy achievement to date?
I was an editor on season 1 of How To With John Wilson (HBO) and also directed a 3-spot campaign for Universal Studios theme parks, which made the kid in me very proud!
When you were coming up in comedy, what helped you stick with it? 
My inner child, and the sense of community. I’ve always had a very close relationship with my inner child, in that she is usually screaming at me! When things aren’t fun, she lets me know she’s cranky. When something is funny, she laughs and heightens whatever is silly about it. My inner child is like a loud, crass, fart-joke-loving clown that I can’t escape, so I embrace her! I also spent 5 years at UCB learning improv and sketch. Then I worked for their production wing as a director and editor. I collaborated with so many funny, talented people who inspired me to reach high.
Have you ever dealt with trolls?
Yup! When it comes to troll-like comments, it’s easy for me to realize that their need to troll my work is not about me, but rather about their own insecurities. But I have had to engage in some sensitive conversations around gender and race with colleagues and my go-to approach is to listen first before deciding if the issue is best as a personal learning experience or a chance for constructive dialogue.
On your deathbed, what transcendent advice would you croak at a young comedian? 
If it’s embarrassing, do it.
How has being funny helped you in your life? 
For me, almost nothing is off-limits when finding light in the dark. I’ve joked about the best and worst experiences, and having a sense of humor about everything makes life so, SO much easier for me. I also use humor to break the ice with every new person I encounter. Especially when I can tell that they are shy or nervous, and it makes me feel so much better knowing that I can use my funny bone to get through the interaction. I truly feel that laughter is healing.
At 32, a friend died suddenly. It was shocking and devastating, but the comedy community I was a part of knew that he would want us to celebrate his life loudly. He LOVED comedy, and he LOVED crass, taboo humor, so we put together a huge comedy show in his honor where we joked about his death and how he was missing the show because it’s what he would have wanted. It was incredibly cathartic and helpful in the healing process.
What specific things should a novice comedy writer do to shape their voice? 
Become a part of a community! Take classes or go out to shows and meet like-minded people and make a bunch of weird shit that fails as well as succeeds so you can see what works! Find your tribe and don’t go it alone, because you don’t have to. Write down anything and everything that you find the least bit funny throughout the day because you never know how it might spark an idea. Say the quiet thing loud! Fuck fear in the bum.
Was there one person who inspired you to go into comedy? 
Pee Wee Herman! (aka, Paul Reubens) What a beautiful freak. As a kid (and now as a post-kid), I marveled at Pee Wee’s bold flamboyance and creativity. He gave me the permission to be a giant weirdo and have fun with the strangeness of life. I watched Pee Wee’s Playhouse on Saturday mornings and my dad would tape it on VHS so I could watch it over and over and over again. I still feel very connected to his love and expression of art, color, music, and multi-media.
What is your go-to show when you’ve had a bad day?
Star Trek: The Next Generation! It’s not a comedy, but I LOVE sci-fi, and the show gives a unique sense of positivity and hope for a brighter future, and the core cast/crew are the best examples of teamwork! Movie-wise, the original Ghostbusters or Beetlejuice will always make me feel at home.
What single word always cracks you up?
“No”, but said with a thick Australian accent, like “Noouar.”