It’s not easy to build a long and lucrative career by making comedy that some people might be tempted to call silly or sophomoric. If it were, more comedians would be as successful as Marlon Wayans. Wayans, the youngest sibling in a family dynasty that also includes his brothers Damon, Shawn and Keenen Ivory Wayans and his sister Kim Wayans, has over the course of his 30-plus-year career scored in nearly every format. He has starred in broad sitcoms (the WB’s “The Wayans Bros.”), irreverent sketch comedy (“In Living Color”) and slapstick movies (“White Chicks”; the first two installments in the “Scary Movie” franchise), and released three, let’s say, Rabelaisian standup specials. His newest effort in that realm, “Good Grief,” will premiere on Amazon Prime Video on June 4.

In that special, Wayans, who has also carved out an impressive sideline as a supporting dramatic actor in films, is branching out by using comedy to work through some seriously heavy emotions. “Good Grief” is all about the death of his parents as well as the nearly 60 other loved ones he has lost in recent years.

When I talked with Wayans, he was in Albuquerque, where he was filming a psychological horror movie for Jordan Peele’s Monkeypaw production company — and, ahead of the first of our two conversations, getting ready to host a party for the cast and crew.

Since you’re having a party tonight, it seems perfectly natural to talk about the subject of your new special: the death of your parents. Isn’t that crazy? Other people are like, What’s your next special? “Oh, it’s a funny journey about the death of my parents.” But it wasn’t just the death of my parents. I lost 58 people that I loved in a matter of three years. It felt, like, biblical.

How do you find the funny thing in the sad thing? It’s been a gift since I was a kid. I mean, all of us Wayanses, we’re crazy people. The worst thing happens, and the first thing we’d think is What’s funny about it? I remember when my cousin Ceddy died and my auntie buried him in jeans and a T-shirt and some Air Force 1s and a baseball cap. Damon looks and goes, “If there’s a dress code in heaven, I don’t think Ceddy’s getting in.”