Rain was pouring down and the skies were gloomy on a spring night in New Haven, but inside the Shubert Theater it was all smiles and laughter.

Brian Regan, a veteran stand-up comedian, performed an hour-long set in front of a sold-out crowd on Friday, April 26. Regan, who perhaps is best known for his routines that have gone viral on YouTube on everything from his third-grade spelling bee to little league baseball, performed some brand-new original material.

Gary Brightwell set the tone for the night with an impressive opening act. Brightwell, a former aerospace engineer, quit his day job to pursue stand-up comedy full-time and has done quite well for himself since. He is a regular on Sirius/XM Satellite Radio, and he has been an opening act for Jerry Seinfeld and Jay Leno in addition to Regan.

Brightwell mostly joked about his girlfriend moving in with him back home in Los Angeles. He mentioned how she wanted to throw out things they no longer needed, but that it skewed towards things she felt they did not need. That included throwing out his bobblehead collection, which came full circle when she expressed her concerns about how she would be able to tell if there was an earthquake. “I used to look at my bobbleheads!” Brightwell yelled to a roar of laughter. Shortly after, Brightwell introduced Regan and stepped aside.

Regan was dressed in a button-up covered by a suit jacket and jeans. He gave little to no introduction and did not mention anything about the venue or the area. In fact, if you had seen a recording of the show, you would not even be able to tell it took place in Connecticut. That’s the magical thing about Regan, though. His material plays anywhere and with anyone.

Since there was such poor weather on Friday night, a large majority of the crowd arrived when the doors to the lobby had opened. It was not hard to notice the incredible range of ages from middle schoolers to senior citizens. Everyone was buzzing with excitement, as even when we were waiting for the theater doors to open, I couldn’t help but overhear two avid fans debating which of Regan’s YouTube sets was the funniest.

Regan covered a variety of topics during his set. The only moment the room was silent the entire night was when he paused to have a sip of water on stage. A crowd favorite was when he spoke about the concept of press conferences only mic’ing up the interviewee at the podium and not the interviewer. Regan would mumble to represent the question being inaudible on television to viewers, then respond with a vague answer such as “that was a coaching decision.”

This also carried over into police press conferences, where Regan again represented the question with mumbles, then offered up a response of “we believe that’s the neighborhood the suspect is hiding in.” Speaking of criminal justice, Regan also delved into the phrase “crime doesn’t pay.”

Regan spoke about the nonsense of the quote, rattling off reasons why a person would want to commit a crime, but then adding that after “crunching the numbers” it simply did not award them with any money and wasn’t worth it. In addition, he joked about “if you can’t do the time, don’t do the crime,” and joked about how some prison sentences would take years to complete but that a person could squeeze in a month in the county jail if they really wanted.

Regan, 60, did not shy away from jokes about his age. He also discussed his struggle with sounding relatable on Twitter while also trying to not sound too old and his issue with deciphering emojis of faces people don’t even make in real life.

One of the highlights of the night was when Regan discussed how he recently went to get a massage. He talked about the awkwardness of trying to squeeze his head through the donut-shaped hole and watching the masseuse’s feet. The crowd got into it when he joked, “part of me wanted to see one foot go one way and one foot go the other so I could turn around and see what was going on up there.”

It turns out Regan was at a reiki massage, which is contact-free and about the transfer of energy. Regan quipped back that he doesn’t actually touch his wallet when he pays someone either and that he wished good energy upon her in return.

An aspect that makes Regan so appealing to all kinds of audiences is that he stays out of politics and uses clean language. This allows for both the older folks who aren’t looking for yet another aspect of life to be consumed by politics and the family-friendly audience looking to avoid raunchiness to coexist for the evening, and after Friday night it’s easy to see why Regan has been so successful for so long.