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The last time Pete Holmes saw his friend and fellow stand-up comic Artie Lange he was working on a garbage truck as part of his court sentence. Wearing a New York Giants beanie with a cigarette hanging out of his mouth, Lange, who was charged with heroin possession in 2017 and spent time in jail earlier this year after testing positive for cocaine, told the man filming him on a cell phone, “You’re gonna keep this quiet, right?”

The video ultimately ended up on Lange’s Twitter feed along with a quote from the comedian, who told his fans, “ Nothing wrong with a little hard work. Love you all and can’t wait to be back on stage.”

“To know Artie is to be concerned about him,” Holmes tells me during this week’s episode of The Last Laugh podcast. “And I say that with love. I would say that if he were here.”

“I think he’s clean now, he’s been in rehab,” he adds, explaining that while he knows Lange “wants to get well,” watching his friend struggle with addiction has taught him that there is no question it is a “straight-up disease.”

When Holmes and Judd Apatow were developing their show Crashing for HBO, the original conceit was that the “Pete” character would crash on a different comedian’s couch each week. The pilot of the series is actually titled “Artie Lange” and there is perhaps no better foil to Holmes’ naive, youth pastor-esque character than the hard-partying, foul-mouthed Lange, who is best known for his years as a co-host on The Howard Stern Show.

The creators enjoyed the dynamic between the two comics so much that Lange ended up sticking around, appearing in 11 of the show’s 24 episodes, including what ended up being the series finale this past March after HBO decided to cancel the show.

Holmes tells me he found it “a little bit sad” shooting the last scene with Lange at the Comedy Cellar that comes near the end of that final episode “because Artie was sort of coming undone by that point.”

In the scene, Holmes is hanging out with his new almost-friend and “golden boy of comedy,” as he puts it, John Mulaney—both men are in suits after Pete opened for Mulaney at Town Hall. They sit down at the famous comedians’ table with Lange, who is in his typical backwards baseball cap and track pants. Lange warns Mulaney that he got burned last time he “vouched” for Pete with the club owner and Mulaney makes fun of him: “Oh my god, and most people trust you!” he says with a sarcastic eye-roll.

“It’s not to say that he’s leaving Artie, but there’s sort of this hint of like, well now maybe he’ll go this direction,” Holmes says of his character. “So that sort of broke my heart a little bit to see that image. That was heavy for me.”

His sentiments echo those of Howard Stern, who recently opened up about his professional split from Lange in an interview with The New York Times Magazine’s David Marchese.

“I choose my words about Artie carefully, because I love him,” Stern said. “What’s happening with Artie makes me very sad. We’ve lost touch, and that’s my doing. I got my fingers crossed for the guy. And it wasn’t a clean break. It was many years of wanting Artie to get help.” He added, “I get sad talking about Artie. He was a tremendous contributor. But we had to move on.”

Lange, who opened up about his history of drug abuse during an interview with Mandy Stadtmiller in The Daily Beast last year, was arrested this week yet again, this time for failure to comply with his drug court program.

In general, Holmes says he’s happy with how the show ended after three seasons, but he adds, “If there’s one thing that I wish to make a fourth season for it would be to redeem Artie a little bit more than to have that be the last time we see him.” He and Apatow even discussed a storyline where Pete is “going to the dark side” and Lange has to bring him back to the light. “We thought that was so funny,” he says.

He also teases that there have been some discussions about a possible Crashing movie. “And I was like, I don’t know what the movie would be,” Holmes says, “but if there’s one thing that would be interesting to me it would be that story for Artie.”

This Friday, May 24: Look out for a bonus episode of The Last Laugh podcast from the SXSW festival with SNL writer and stand-up comedian Sam Jay.