Judd Apatow first broke into show business as a comedy writer in the early 90s. He later came into his own as a stand up comic and eventually grew into a kingmaker to countless comedians and actors after evolving into one of the most recognizable directors, writers, and producers in Hollywood.

Beginning Friday, May 20 on HBO Max, you’ll be able to see Apatow’s latest documentary, George Carlin’s American Dream. In the two-part doc, Judd and his crew masterfully share legendary comedian George Carlin’s story.

The documentary, which includes a wide array of rare Carlin footage, pulls back the curtain to reveal the truths, triumphs, and tribulations of arguably the most influential comedian of all time throughout different stages of his career and life.

George Carlin’s American Dream impeccably succeeds in its approach to candidly tell the whole story of Carlin the comic. He wasn’t etched into the Mount Rushmore of comedy the second he took to the stage.

The documentary shows you a legend who struggles, who was virtually down and out of the funny business before a resurgence, and who felt the need to up his game when his Mount Rushmore neighbor, Sam Kinison, began picking up steam in the mid-80s.

“I think that’s what we all admire about [artists] who do great work throughout their entire lives, they’re always looking to what else is happening in the culture. They don't want to be a relic of another era,” Apatow told me over the phone. “So just like some rock musicians heard punk rock and changed what they were doing, George Carlin saw Sam Kinison and thought, ‘Oh, I need to up my game. This is moving in a new direction.’

“And that's why he remained such a big part of the culture up until the end of his life. He didn't just rest on his laurels; he was an artist who tried to dig deeper and take it to the next level.”

Judd and co. also succeeded in depicting what became the comic’s mission onstage, voicing his frustration at feeling “betrayed by the bulls*** in America that’s all around us,” as Carlin puts it himself in the doc.

“I think his main opinion was that the human race has been given some incredible opportunity. The world is so beautiful. It has so much to offer. All we need to do is be kind and share it and take care of each other. And a lot of the time, we do the opposite,” Apatow said of Carlin’s point of view. “And he did say that he felt like somebody who had been let down.

“Early in his life, he seemed much more idealistic and he became much more cynical when he got older and saw that we weren't solving a lot of the problems that he warned people about in the 60s.

“We see that with the environment, for example. He talked about that in the late 60s. And it's how many people weren't talking about it. And even now it requires people like Adam McKay making movies that are about the fact that we refuse to acknowledge how bad problems are getting. And then it is a little bit of what our unfortunate human nature often can be.

“We don't think longterm. We don't want to do something that's the right thing to do now that will be kind to the next generation. We're all about being happy today, and there's an inherent selfishness to a lot of people's behavior and that seemed to drive him crazy.”

In the middle of Carlin’s career, he was at a bit of a crossroads when he began to seem like a stereotype of himself, leading Rick Moranis to do an impression of him on SCTV.

“I think that it was insanely funny. It couldn't be more cutting,” Apatow said of Moranis’ impression. “He did it at a time when some people felt like his material was getting soft, and George Carlin talked about not wanting to be so stressed in this period after he had a heart attack.

“He was trying to not do an act that was about so many negative topics. I think that's what SCTV was going after, the fact that some of the material seemed silly and shallow.

“The funny part is that he reacted against it by going much darker and deeper. So in a way, you could say the criticism from a certain corner, and being inspired by people like Sam Kinison who were going very hard, was the fuel that led to all the good [bits] he did in the last 20 years of his career.”

So which Carlin era was the best?

“I think the great thing about George Carlin is his prime is whatever you enjoyed the most,” Judd said. “A lot of people liked him on the variety shows in the 60s being silly and doing ‘The Hippy Dippy Weatherman’.

“I remember growing up and listening to Class Clown and hearing him dissect words and talk about what it was like being a funny kid at school. And it inspired me and made me want to be a comedian.

“And some people loved the prophetic, dark routines about this country, and what he thought was going wrong. So it's really a matter of taste, but there are very few people who reinvented themselves in comedy as many times as him and succeeded each time.”

One could surmise Carlin reinvented himself one more time, posthumously, as the comic we should have truly listened to in between laughs, a soothsayer who finished his career with an unrivaled batting average.

“I was asked to do [the documentary] before the pandemic, and at that time most of these issues that we discussed in the documentary were happening, debates about freedom of speech, a lot of topics that George Carlin was concerned about, corporate control, politicians, Big Pharma, gun control, women's rights... All of it was in the routines that kept trending on Twitter,” Apatow said.

“So even though George Carlin had been gone since 2008— it seemed that every week he would trend because he had the best bit about what was happening in the country. And that's part of what interested me in working on this project because most comedians' acts age very badly and the material becomes meaningless very quickly. But it was the opposite with George Carlin's material.”

Having worked primarily on feature films, Apatow notes that similar to features, when you’re piecing together a doc, you have to unravel the material to find the story.

“There are elements that are similar to feature films because you are trying to figure out what the story is,” Judd said. “When you make a documentary, you watch all the footage, and you take a look and a listen to everything that exists, and we attempt to discern the story in all of that. It takes a long time to figure it out, and you hope that you're correct in this case.

“We were working with George Carlin's daughter, Kelly Carlin, and his brother Patrick, who sadly just passed away. His manager, Jerry Hamza, was very helpful, and they helped educate us as to what his private world was like. George Carlin didn't do jokes about his marriage and being a father; everything was observational.

“None of it was personal in the later part of his life. He talked about his childhood a little bit, but he never even said he had a kid onstage. So all that was new, and we had to figure out what that story was, and it turned out to be both a beautiful and, at times, harrowing story of a marriage and addiction and two people trying to figure out how to make a relationship work through all of this success and madness.”

Early in Judd’s career, he worked as an executive producer on NBC’s Freaks and Geeks (1999-2000). Following the show’s short run, Apatow began plugging actors from Freaks and Geeks like Seth Rogen and Jason Segel into his feature films like Knocked Up (2007) later on.

“I think there's a rich tradition of mentoring in comedy. I think that that's part of the lineage and I know Judd was mentored; I think it's part of the deal,” Segel told me last month. “I've certainly felt really really lucky and blessed to be a part of that.

“I also think there was at least for us, a bit of a Monte Cristo’s revenge streak about helping us all out because when they cancelled Freaks and Geeks, I think Judd was like, 'You're wrong, I'm right and I'm going to systematically make each one of these people stars to show you how f***ing dumb you are.'”

Apatow weighed in on why he continued backing Freaks and Geeks actors after the show’s demise.

“On one level, I thought the show didn't get the time to explore all of the stories and talents of the people who participated in it. And then on another level, I was just creatively in love with so many of the people who were performing on the show and wanted us to explore what they were all capable of.”