Chocolate Sundaes Comedy is discovering your new favorite comics

The first time you walk into a venue, the murmurs of the crowd, the nervous hum of anticipation before the show starts—all of it becomes more and more electric as the countdown winds down. Lights go down, the spotlight comes up, and laughter becomes a gateway to a communal experience, one that can stretch beyond that night.

That’s because when someone’s on stage, you never know where they’ll end up. But for many of your favorite comedians, they all seem to start at the same place: Chocolate Sundaes Comedy.

Founded by executive producer Pookey Wigington in 1999, Chocolate Sundaes takes place at one of comedy’s most sacred sites: the world-famous Laugh Factory in Hollywood, California.

“It’s an urban comedy show—that’s the chocolate part—but the ‘Sundaes’ part is [because] all cultures are there,” explains Lani Crooks, the show’s long-time producer. “You have the vanilla ice cream, you have the banana, you have the caramel… It’s a blending of all cultures.”

The weekly event has been a staple for lovers of comedy for over 20 years, and its digital footprint brings the show to people who can’t make it to Sunset Boulevard: 150K+ followers are tapped in on TikTok, 250K+ on Instagram, and more than 600,000 subscribers on YouTube. It all starts, funnily enough, on Sundays.

That time is spent working with her team remotely, reviewing finances, getting W9s and talent release forms signed via Dropbox Sign, and booking comedians. She also spends time managing their marketing growth and reviewing content on Dropbox—videos of every comedian's set at Chocolate Sundae. Here, comedy is king and content is its heir.

“A lot of people know about us, and still a lot of people have never heard of us. So that's [why] we're really trying to push the content and get our brand out nationally,” Crooks says.

That success not only impacts the show but the comedians themselves. Sharing sets on social media helps a new generation of comedians launch their careers, illustrated by all the working comedians turned celebrities who still drop by for laughs and sets.

Crooks talks to us about how Chocolate Sundaes uses social media to push the future of comedy forward.

Why is content creation so important to Chocolate Sundaes?
To put butts in the seats, you have to market the show—and there’s no other way that we would be able to market a comedy show without showing comedy. Plus taking that content and putting it on YouTube and Facebook and these other places drives revenue.

We wouldn’t be able to do that without content, and we wouldn’t be able to do that without the butts in the seats. That would look awful: to have content online with a comedian performing and nobody in the crowd laughing. So the whole business is fueled by content.
 

How do you take what’s in the show and distill it for social?
The videographers upload all of our footage to Dropbox. We organize files by date—we have the year, then inside each year are months, and then inside that the week. We also might copy the file into a YouTube or social media folder.

File-sharing is so important to our workflow because we all work remotely. If we couldn’t do that, we’d have to pass around hard drives. 

Dropbox helps us save time in the content-creation process with how easy it is to share and collaborate. Our workflow is never interrupted by a Dropbox issue. It works seamlessly, and that is really important, because some people have issues with some of our other software.

I have a full-time editor that'll download everything to her hard drive, and then goes through and edits everything. We have about three to four hours of footage a week that we get from the shows, and we’re cutting probably 15-20 pieces of content per week. She’ll upload all of that back into Dropbox.

I understand the context of everything because I watch the shows, so being there definitely helps on the edit. I spend my days laughing, watching footage. Our communication is all over the place. We’ll talk about edits on Slack, on text, on email. We use the timestamp comment feature in Dropbox a lot when discussing edits with each other. That’s super helpful versus having to type out timestamps.

It sounds like the content gets “butts in seats” for Chocolate Sundaes and helps out your talent.
Comedians will ask for copies of their set now, so we'll upload those and share them with Dropbox. We've had comedians whose clips have blown up, that have changed their lives, from getting them booked all over the country to booking America's Got Talent. They use our YouTube channel all the time to discover comedians.

And so many comedy clubs and shows steal our clips too to promote comedians for their clubs. I don't mind because ultimately, it's helping the comedian. A lot of them get paid off ticket sales at these clubs, so if I help them sell more tickets, then I'm with it. We want all comedy clubs and all comedians to succeed.

Do you have any favorite clips from recent shows that stand out to you?
Probably one from BT Kingsley: He had a joke about [Kendrick Lamar diss track] “Not Like Us” that we posted and it went kind of viral. He talks about how… I can't explain it! You know, these comedians are geniuses.

Whether it's in person or on social media, what do you want people to take away from your club?
That it's a place for any and everyone to come and laugh and have a good time. We'll have an 80-year-old white grandma from Indiana sitting next to a 20-year-old Black couple from Inglewood. And we make fun of everyone. Like everyone can get roasted—no one is safe. That's how we show love.

This interview has been edited and condensed for clarity.