Gary Goldman knows he gets laughs by subverting your expectations.

He's a big guy, 6-6 with an athletic build.

He played football on scholarship at Boston College.

But on stage, his eyes twinkle and his smile broadens most widely

when he lands a joke with an obscure literary reference or unexpected

wordplay. Vulnerabilities are also celebrated in Gary's comedy, especially his own, like his

depression, including a severe bout in his 40s that led to his special called The Great Depression,

or about growing up poor, which Gary explored in his special last year called Born on Third Base.

We are big fans of Gary Goldman's comedy here at Death Sex and Money.

Producer Cameron Drews described his specials as so well-crafted and that in this conversation, you hear a little bit of the id behind all that.

He and I talk about growing up as a sensitive boy after his dad left the family and his older brothers enforced a rigid brand of 70s and 80s, Massachusetts masculinity.

And Gary and I talk about how that shapes his comedy that righteously celebrates the underdog

and explores the long tale of bullying

and the ways men police each other's behavior.

We also talk about his latest show, which is a celebration of bookishness and words

and becoming a nerdy kid who likes himself.

He called it grandiloquent.

Basically, I say, for 31 years, the subtext of my act has been, no, listen to me, I'm pretty smart, right?

And that I'm bombastic, oratund, and darn near grandiloquent, I say.

Like, I go over every word in my set,

and when I looked up the definition for grandiloquent,

it seemed to fit me to a T.

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