Ali Regan adds whimsy where she can - GOLD Comedy - Make Funny Stuff

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Ali Regan adds whimsy where she can

GOLD Editors Jul 24, 2025

Ali Regan a muti-disclipinary artist based in NYC. She’s a BFA alumnus from NYU Tisch Drama with two minors: Business, Entertainment, Music, Technology and Producing. New Studio on Broadway, Stonestreet Studios, and a semester at the Royal Academy of Dramatic Art were my training centers. Ali currently performs with Drunk Shakespeare.


What were you like as a teen?

I was super focused on getting everything right all the time. Which, in hindsight, I of course wish I wasn’t. I was determined to do things right and never make a mistake. That being said, I made mistakes all the time because they are unavoidable and I often connected to my peers through shared niche interests and, at the time, topical internet references. I cared more to be liked than to be likable, if that makes sense. I was a goofy teen who moved between freshman and sophomore year of high school form a co-ed public school to an all girls private school – so I kind of had my work cut out for me there.
Did you have an un-sexy starter job?
I’ve had plenty of jobs over the years – I’m still pretty early in my career even now but I would say something “un-sexy” was working as a COVID monitor and COVID manager during the pandemic. I was in “cool” places like Broadway or SNL–but still would be testing people and having to be a stickler about masking, and generally feeling like the one reminder of the terrible things happening. That un-sexy-ness led me to the challenge of how to make the most out of the worst and still connect with people even when I had to tell them something they didn’t want to hear.
What’s your biggest comedy achievement to date?
Working at Drunk Shakespeare performing 8 shows a week–no doubt.
When you were coming up in comedy, what helped you stick with it? 
My teachers, friends, and honestly, silly video compilations and internet comedians that inspire me. People, places, and things that remind me that it’s okay to be silly goofy and sometimes that IS enough.
Have you ever dealt with trolls?
Yes and (I dealt with it) by doing the best I can not to attach my self-worth to my output.
On your deathbed, what transcendent advice would you croak at a young comedian? 
Oh my gosh, take a fucking breath. You’re better than you think.
Best comedy advice you ever got?
Just be.
Worst comedy advice you ever got? 
You need to always be prepared.
How has being funny helped you in your life? 
Trauma. Humor coming from trauma. Getting through trauma with humor. Reflecting over years and still being able to find something to laugh about. Not just as a shield or deflection, but as a perspective.
What specific things should a novice comic do to shape their voice?
Try to write music or study music in some capacity. Maybe just find some music you love and try to understand why you love it.
Was there one person who inspired you to go into comedy?
I wouldn’t say just one person – probably a collection of people over time.
What is your go-to show or movie?
Mmmm, it changes. I’d say I like to rewatch my favorite movies/comfort movies. I also enjoy watching reviews of horror movies on this YouTube channel called “Foundflix.”
What single word always cracks you up?
Pretty much any nonsensical outburst.
Final thoughts?
Add a little whimsy where you can.

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