Gary Gulman aims to deliver big laughs in ‘Born on Third Base’

By Marianne Garvey, CNN

(CNN) — Gary Gulman is at the top of his game in his new Max special, “Born on Third Base.”

The comedian tackles growing up poor, income inequality, Pop-Tarts, shady dentists and rude Chipotle customers, among other topics, in the set. One masterful joke near the end of the hour-long special weaves basketball and magic together so well, it’ll leave you slack-jawed over Gulman’s joke-telling skills.

“I definitely think it’s my funniest [special],” Gulman told CNN. “I think ‘The Great Depresh’ is probably my most meaningful and I still get emails and comments every day on that and it’s four years old now, so that was really special. But this is definitely my funniest.”

Gulman made “The Great Depresh” comedy special in 2019. It covers the crippling battle with depression he suffered before the right mix of doctors and medication helped him recover while living back at home with his mom.

In the new special, he looks happy and is eager to share his jokes, some which he’d written during that time. He said they didn’t exactly fit in with jokes about receiving mental health care, so he saved them for when he was in a better place.

“I had a lot of the jokes from the Chipotle routine, and then also I had the hockey routine, and it just didn’t fit in thematically for the ‘Great Depresh.’ So [with this special] I started with those two,” Gulman said. “Then I saw a tweet asking what comedians were talking about class. And I remember thinking that I couldn’t think of any comedians who were talking about class. Which doesn’t mean that there aren’t any, it just hadn’t intersected with my eyes.”

He thought it was a great opportunity to try something that not many people have done, explaining how growing in poverty and on public assistance strongly shaped his views on the topic.

“I saw that as kind a cool challenge,” Gulman said. “I’ve spent most of my life thinking about and considering the effects of poverty and need on the community and also on myself at different stages in my life, especially my childhood.”

The topic isn’t going to get dated any time soon, he said, because income disparity “keeps getting worse and worse, and we’re being more and more affected by people in power with ungodly amounts of net worth.”

Surprising punchlines

On the topic of net worth, Gulman takes a swipe at fellow comedian Jerry Seinfeld – and his massive wealth. He knows some people will find it “controversial” that he mentions the comic in the special.

“I didn’t want it to be too mean or anything like that because he is a beloved figure. I just think his priorities are out of whack. And also he’s just a great representation of the income inequality in this country and happens to be ostensibly a person in my business, but really not in the same business.”

Gulman transitions his bit about Seinfeld into a joke about Pop-Tarts, a topic Seinfeld has attempted to tackle himself. And yes, it was intentional. Not to prove he could make better jokes on the topic, but to talk about what the frosted treat means to kids who are on free lunch.

“I remember how big a deal that New York Times made out of him creating that bit,” Gulman said. “And it wasn’t so much that I wanted to do it better, I just wanted to show the other side of that and what Pop-Tarts mean to kids in need or on free lunch.”

Gulman wraps up the special with a joke comparing his basketball skills to a close-up magic trick he once witnessed. It’s a grand finale with a very unexpected curse word.

“It’s important to maintain an element of surprise with a lot of jokes,” Gulman said, “And that was the case with that one. It’s almost like you want the punchline to be the last thing somebody would predict or expect.”

“Born On Third Base” streams on Max Dec. 21.

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