Born and raised in Boston, Kendra Cunningham has built a career out of sharp observational humor, fearless storytelling, and an unmistakable comedic voice. What started with a childhood story about Snoopy—carefully preserved by her grandmother in a three-ring binder—grew into a multifaceted career spanning stand-up, television, screenwriting, essays, and digital comedy.

Kendra has appeared on Last Comic Standing and The Tonight Show Starring Jimmy Fallon, performed at festivals including Just for Laughs, the Boston Comedy Festival, and the Glasgow Comedy Festival, and released acclaimed stand-up specials including On My Best Behavior and Meatball Therapy. Her essay blog Blonde Logic was quoted in The New York Times, her jokes were named among the Top 100 on Last Comic Standing, and her original pilot Swagger won Best Screenplay at the Flickers’ Rhode Island International Film Festival.

In addition to writing thousands of jokes, essays, and dozens of award-winning web series, Kendra is available for ghostwriting, punch-ups, script writing, joke writing, and comedic consulting of all kinds.

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What were you like as a teen?

I liked being overdressed and in charge.

Did you have an un-sexy starter job?

I have been a bartender off and on all my life. An  executive assistant. A teacher. A forensic case manager. I even sold Kenworth 16-wheelers for a while. (I didn’t sell any.) 

What do you consider to be your biggest comedy achievement?

That is a tough one. Different things matter to me for different reasons. I will say Last Comic Standing because I got to be around Wanda Sykes and she liked my joke writing 

When you were coming up in comedy, what helped you stick with it? 

The challenge of new material.

How do you handle trolls and hecklers?

Disassociate.

On your deathbed, what transcendent advice would you croak at a young comedian? 

Don’t take it too seriously. Have a full life beyond comedy.

Best comedy advice you ever got?

Have fun! when you are having fun on stage- its contagious 

Worst comedy advice you ever got? 

Do as many sets per week as possible.

How has being funny helped you in your life?

I grew up in a funny family. Funny has always been a coping mechanism for life’s ups and downs.

What specific things should a novice comic do to shape their voice? 

Talk about issues or topics they sincerely feel strongly about.

Was there one person who inspired you to go into comedy?

My mother.

Do you have a writing routine?
I’m writing things down all the time and then coming back to the idea when there is more time for me to process it.

What is your go-to show?

Right now? The Comeback with Lisa Kudrow.

What single word always cracks you up?

Dingleberry.