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Happy Medium’s Jeff Stevens Inspires by Bringing Laughter Behind Prison Walls

Jeff Stevens says performing for inmates is rewarding.
ShreddER July 6, 2026
Happy Medium's Jeff Stevens Inspires by Bringing Laughter Behind Prison Walls
Credit: Jeff Stevens; Happy Medium

Happy Medium Skateboarding's very own Jeff Stevens has been staying busy lately.

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YouTube: A Happy Medium Skateboarding

Along with filming clips and spending plenty of time skating in the streets, he has also been performing stand up comedy in places that most comedians never get the chance to visit.

Stevens recently shared that one of the most meaningful performances he has ever done took place inside a prison.

While many comics dream about packed comedy clubs and theater shows, Stevens said the experience of performing for inmates stood above everything else.

According to Stevens, what made the show so special was the audience itself. He explained that inmates were not afraid to laugh or worried about how the people around them would react.

Instead of holding back, they enjoyed the moment and responded naturally throughout the performance.

He compared that to many comedy club audiences where people sometimes hesitate because they are concerned about what others might think.

Stevens also joked that the prison crowd was a literal captive audience, but he made it clear that the real reason the show meant so much had nothing to do with that.

It was about seeing people genuinely enjoying themselves and sharing a few moments of laughter together.

He ended his post by thanking Kerry Wells for making the opportunity happen, giving credit to the person who helped bring the performance to the inmates.

It is not every day that someone from the skate community spends time giving back in a setting like this.

Stevens Posted:

"Out of all the venues I’ve played, performing at the prison has been the most rewarding. And it’s not just because they’re a literal captive audience. Unlike standard comedy club crowds, inmates aren’t afraid to laugh or quick to get offended. In regular clubs, people often hold back because they’re worried about what the person next to them thinks. In prison, that filter is completely gone. Anyways I wanted to give a big thank you to @kerrywells311 for making this all possible!"

View this post on Instagram

A post shared by Jeff Stevens (@jeffstevens)

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