Carolina Montesquieu turns the wig around and sings it out

Carolina Montesquieu is a Dominican-American standup comedian. Growing up near Lawrence, MA in a vibrant Dominican community, she is deeply connected to her Caribbean roots. Her standup blends real-life stories, cultural chaos, and unforgettable punchlines with a touch of darkness and reflection. It’s a buffet of emotions that captures the essence of her unique perspective, combining her Dominican heritage with her experiences growing up in a white Y2K-influenced environment. Carolina’s comedy offers a blend of cultures and eras, resonating with a wide audience.

Carolina began her stand-up comedy journey in July of 2022. In the past year she has performed over 400 times, making her mark in the Boston scene and establishing herself in New York. You can catch her at venues like Laugh Boston, The Stand NYC, and festivals nationwide. She has opened for Vlad Camaano, and Radel Ortiz. Most recently, Carolina set a record for most tickets sold at Lil’ Chuck comedy club in Boston with her debut headlining show, delivering a laughter filled 42 minute set. Whether performing for a room full of Dominicans who get every reference or a mainstream audience experiencing her for the first time, Carolina’s dynamic presence and undeniable talent captivate every crowd. This is just the beginning. Come see for yourself.

What were you like as a teen?
Been funny my whole life
Did you have an un-sexy starter job?
Debt collector, finance, car sales…
What do you consider to be your biggest comedy achievement to date?
Getting into the finals of the 1st don’t tell comedy competition
When you were coming up in comedy, what helped you stick with it? 
Outside validation for sureeee. The universe was agreeing with me.
Have you ever dealt with trolls? Hecklers? 
At least a dozen white men have said to my face that I’m moving up and they are not because I’m a Hispanic woman. I just say, “Yeah, but you also have to be funny.”
On your deathbed, what transcendent advice would you croak at a young comedian? 
“Anything you do, let it come from you, then it will be new.” – Stephen Sondheim.
Best comedy advice you ever got?
“Record, edit, record.”
Worst comedy advice you ever got? 
“Don’t talk about Dominicans…people don’t know what that is.”
How has being funny helped you in your life? 
I used to use it as a tool to make people feel comfortable being mean to me..but now I use it to make people feel uncomfortable!
What specific things should a novice comic do to shape their voice?
Listen to the audience carefully and slow down.
Do you have a writing routine?
Not too strict. But identifying a new joke has become easier for me. If I question something or make someone laugh in a conversation, I bring it to the stage
What is your go-to movie when you’ve had a bad day?
Dream Girls; I know EVERY word. Sometimes you just have to turn the wigs around and sing it out.
What single word always cracks you up?
Hyperpigmentation.