Michael Che tries not to impose too many rules on his fellow writers when they’re creating sketches for his HBO Max comedy series, “That Damn Michael Che.”
“We’ll write what we think would be the funniest chain of events,” he explained recently. Yet for all the paths this would seem to leave open, their sketches — about the tribulations faced by a fictionalized version of Che — inevitably end at a similar destination.
“I always come out looking bad,” he said. “I’m never the winner.”
With a chuckle, he added that he understood why having his own series required these outcomes. “When you invite people to your house, you always eat last,” he said.
In the sketch that opens the second season (due May 26), our star tries to help a man getting beaten up on a subway platform. But when the victim starts spouting bizarre obscenities, Che becomes the target of an internet backlash that threatens to wreck his career.
The episode that ensues is (among other things) a parody of the “John Wick” movies and a satire of now-familiar rituals of so-called cancel culture as Che fumbles to restore his reputation.
In contrast to the rapid-fire, headline-driven setups and punch lines that Che has delivered for eight seasons as a Weekend Update anchor on “Saturday Night Live,” “That Damn Michael Che” offers a looser blend of standup and sketch that gradually becomes a story or riff on contemporary themes.
That his streaming series has arrived at this broad formula — applied to quotidian annoyances, social injustices and high-class celebrity problems — was “not necessarily on purpose,” Che said.
“I think that ended up being what happened,” he explained. “When you start a show, you’re looking to find its identity.”
It’s a process that Che continues to navigate, not only on “That Damn Michael Che” but also in his standup and on “S.N.L.,” where he is learning to balance the demands of these intersecting assignments. He is still discovering the individual benefits of these formats, the best ways to work on them and even what he wants to say in them.
While Che projects a certain unflappability in his live comedy, he can be self-scrutinizing offstage and openly unsure about his choices. If you squint a certain way, you might even see a guy at a crossroads, who has at least teased — then quickly laughed off — the idea of ending his productive “S.N.L.” tenure.
As with developing a new series, Che suggested that figuring himself out professionally had also required trial and error. “Everything looks easy till you start doing it,” he said.
On a Tuesday afternoon this month, Che, who turns 39 on May 19, was sitting in his “S.N.L.” dressing room, a darkened chamber lit by a TV silently playing “Teenage Mutant Ninja Turtles II: The Secret of the Ooze.” He was initially quiet and hidden under a hoodie — still reacclimating after a trip back from the Netflix comedy festival in Los Angeles, he said — but he became more gregarious as the conversation turned to his work.
Though the cycle of another week at “S.N.L.” was underway, Che said he wasn’t stressed. “I like the dirty part of the game,” he said, by which he meant composing material: “Trying to crack the code, solving the puzzle. The part nobody sees is what’s really interesting to me.”
That work ethic caught the attention of his colleagues at “S.N.L.,” where Che started contributing as a guest writer in 2013 and joined Colin Jost on the Weekend Update desk in the fall of 2014.
Jost, who helped bring him onto the show, said that Che quickly became one of its best writers despite his lack of previous sketch-writing experience.
“He just worked at it and figured it out,” Jost said in an email.
Lorne Michaels, the creator and longtime executive producer of “S.N.L.,” said he didn’t see any neediness in Che’s coolly confident stage presence. For most performers, Michaels explained, “it’s all about being loved or wanted, and he doesn’t seem terribly interested in that.”
He added, “If he believes in the joke, he’s doing it. And he’ll acknowledge the audience’s response, but you don’t get the sense that he’s not going to sleep that night.”
Jost said that while working with Che on Weekend Update, it “definitely took a while for us to figure it out, individually and together, and that’s why it’s satisfying now to be out there and get to enjoy it after years where it felt like a struggle.”
“Che’s thing was always that he didn’t want to tell a joke that someone else could tell,” Jost said, adding that he believes Che had accomplished this: “Even a random joke at the end of Update that anyone could technically tell, he finds a way to do it that’s unique to him.”
From one perspective, Che’s ascent has been rapid: after playing his first open mics in 2009, he was performing on David Letterman’s “Late Show” in 2012 and working as a correspondent on Jon Stewart’s “Daily Show” two years later.
But for many years prior, Che cycled through other vocations: drawing and painting, designing T-shirts, working in customer service at a car dealership. All he wanted out of a career, he told me, was that it “wasn’t illegal or a gigolo.”
His upbringing as the youngest of seven children raised in public housing on Manhattan’s Lower East Side is rarely far from his mind, and he frequently looks for ways to give back to the community that forged him.
When I asked him, somewhat frivolously, what he’d do to keep pace with Jost’s recent investment in a retired Staten Island ferryboat, Che thought for a moment. Then he answered that he’d use a hypothetical windfall to renovate a community center at the Alfred E. Smith Houses that he frequented in his childhood.
“Having more places and programs for kids to go would help them a lot,” he said. “Sometimes you can’t just go home. Sometimes there’s 12 people living in a three-bedroom apartment. Sometimes there’s bad things happening in your apartment.”
He drew a breath and said to me, “That’s a very odd question.”
When the opportunity arose for Che to create his own series with HBO in 2020, Michaels encouraged him to pursue it in tandem with his “S.N.L.” duties. “It’s in my interest for people to keep growing,” said Michaels, who is also an executive producer on “That Damn Michael Che.”
But working out what the new show would be was a challenge. Che said he originally thought it would be an animated narrative — an idea he said he might still return to — then leaned back to sketch comedy, which is faster and more familiar to him.
“As the scripts started to come in, HBO started saying, it’d be great if you were on camera a lot more,” Che said. With his existing commitment to “S.N.L.,” Che said the questions he faced were, “What could we shoot? What could we do without having to miss work here?”
Hiring a writing staff for “That Damn Michael Che” wasn’t difficult; the star just turned to the cadre of stand-ups he regularly hangs out with in comedy clubs.
“Those late nights, talking about nothing, goofing off, turned into Mike getting his own show and saying, ‘Hey, come write,’” said Reggie Conquest, a comedian and actor (“Abbott Elementary,” “Scream”) who has written for both seasons of the series.
As Conquest described them, those writing sessions “felt just like hanging out at a comedy club and talking like we normally do.”
“It was very therapeutic,” he said, as they spoke “from real places, real experiences. And no matter how awful it might sound, you try to make it funny.”
In Season 1, that strategy yielded sketches on topics like police violence and hesitancy around the Covid-19 vaccine. Reviewing the show for The Daily Beast, Kevin Fallon wrote, “The comedy and the intimacy of Che’s personal experience create a show that feels funnier, more resonant, and more current than he could ever hope to be on ‘S.N.L.’”
Gary Richardson, the head writer of “That Damn Michael Che” and an “S.N.L.” veteran, said that the first season reflected the interests and preoccupations of its star. “He really wanted to make sure it was his show,” Richardson said. “It was a lot of pressure-testing his ideas.”
On Season 2, Richardson said that Che “let other people cook more — he felt more comfortable opening it up and letting other folks add their flavor to the pot.”
Che himself said his approach this season was to aim “more on the side of funny than on the side of making a point.” That has led to episodes where he tries to organize a brunch party honoring Black excellence and struggles in his shameless efforts to populate it with top celebrities; and where he confronts the repercussions of cancel culture, a phenomenon that Che said he doesn’t regard as meaningful or particularly new.
“I don’t buy into it,” Che said. “To me, there’s risk in everything you say and you have to take responsibility no matter what. It’s funny for me to see people learn things that I had to know as a survival tactic my entire life.”
In his own work, Che said, “I constantly think my career is over after a bad set or a bad Update. You always think, this is it, at any moment, I’ll be found out.” By having it happen to him in a sketch where an attempt at altruism leads to his downfall, he said, “I just thought it would be a very funny way to lose everything.”
Not that Che expects to give up his habit of using social media to antagonize journalists who have criticized him or who he feels have misrepresented him or his friends.
“I haven’t turned over a new leaf,” he said. “There is a power that I think writers know they have, that they won’t admit they have, in making perception a reality. I just like to make fun of that. It’s like, I see you — you see me.”
Che admitted to a certain professional jealousy of peers like Dave Chappelle, Bill Burr and Michelle Wolf, whom he sees as especially polished stand-ups who can devote their time solely to honing their live acts.
It would be understandable if Che were contemplating a life after “Saturday Night Live,” where he is the first Black person to become a head writer and the first to be an anchor on Weekend Update. He holds the second-longest tenure in the show’s history (behind his desk partner, Jost).
When Che made a pop-up appearance at a Minneapolis hair salon in March, the Minneapolis Star Tribune quoted him as saying, “This is my last year.” But in comments he later posted to his Instagram account, Che said that he wasn’t leaving the show.
(In the post, which he has since deleted, Che wrote: “to comedy fans; please stop telling reporters everything you hear at a comedy show. youre spoiling the trick.”)
In our conversation, Che continued to play his remarks off as a joke. “Who doesn’t say they’re going to quit their job when they’re at their other job?” he said. “I’m sure Biden says that twice a week.”
In a more sincere tone, Che said, “My head has been at leaving for the past five seasons.”
He added, “I do think that I’ve been here longer than I’ll be here. This show is built for younger voices and, at some point, there’ll be something more exciting to watch at the halfway mark of the show than me and dumb Jost.”
(Jost said he construed that as a term of endearment. “Now I’m excited to pitch ‘Dumb Jost’ to Apple,” he responded.)
Michaels said that “a year of change” was possible after the current season of “S.N.L.” but he hoped Che would not be part of that turnover.
“If I had my way, he’ll be here,” Michaels said. “And I don’t always get my way. But when you have someone who’s the real thing, you want to hold on as long as you can.”
Though the comedian hopes his work on “That Damn Michael Che” will stand on its own, Che recognized that his time at “S.N.L.” confers a unique status that no other program can duplicate.
“There’s people who hate me who can tell me every joke I’ve ever done on the show,” he said.
He added, “Even when it’s not exciting, people are like, when’s it going to be exciting? No one says it was never exciting. You understand that, at any moment, something cool could happen.”
Speaking as a guy who already has two sketch shows and a standup act to choose from, Che said, “I got really lucky in my career. When I get bad stuff, I’m like, ‘Yeah, I’m due, I can’t complain.’ I didn’t complain when it was good.”