It would be perfectly reasonable to assume that debuting at the tail end of the most wildly unpredictable presidential election in modern times would provide Saturday Night Live with all of the drama it can handle as it celebrates its hotly anticipated 50th season. But drama often lurks behind the scenes, too, as it has with the will-he-or-won’t-he retirement rumors surrounding TV maestro Lorne Michaels. In the fall of 2020, it was Michaels who appeared on Sunday Today and revealed that the 50th season would be his last. “By that point, I think I really deserve to wander off,” he told host Willie Geist.

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The comment, which he then doubled down on in subsequent interviews, prompted a tireless succession of media stories about who might replace him. Tina Fey’s name emerged, along with that of Seth Meyers, Colin Jost and Michael Che. Then something happened as the milestone season approached: Michaels decided that he didn’t actually want to leave the show he created 50 years ago and has been fastidiously lording over for the past half-century, save for a brief window in the early 1980s. Sure, he’d scale back as he prepares to turn 80 later this year, but the man who has launched the careers of Adam Sandler, Chris Rock, Will Ferrell and Kristen Wiig — among many, many others — still loves the sketch series and its command of the zeitgeist, particularly during political periods. “It’s always going to be described the same way, which is ‘uneven,’ and yet people have decided somehow that it’s important,” Michaels says now. “And so as long as it’s important and I can be useful, I’ll stay.”

SNL’s Weekend Update anchors Colin Jost (as Kamala Harris) and Michael Che (as Donald Trump) were photographed Sept. 10 at PMC Studios in New York.

Photographed by Gavin Bond

Like most everything on television, SNL has seen its linear ratings slide in recent years, but it remains the No. 1 entertainment series in the still important 18-to-49 demo and, despite its five decades on the air, feels tailor-made for the clippable, shareable social media era. In fact, SNL’s most recent season generated 3.1 billion social video views. Even without a fresh variety series trophy, which it lost to John Oliver, it’s the most decorated show in Emmys history with 103 wins. And the forthcoming season, which kicks off Sept. 28, should gin up plenty more attention, both because of the election, which will bring back Maya Rudolph as Kamala Harris, and the season-long 50th anniversary celebration, punctuated by a star-studded event at Radio City Music Hall in February and a reunion episode featuring a who’s who of SNL’s past. There’s also a buzzy Jason Reitman film hitting theaters in October, which serves as a behind-the-scenes reimagining of SNL’s first episode and a love letter to Michaels.

Over the course of a week in mid-September, Michaels and his “Weekend Update” anchors, Colin Jost and Michael Che, spoke separately on multiple occasions about the perks and perils of political comedy in today’s fractured America, a future without Michaels and what to expect from SNL’s 50th. 

This being the 50th season, does that come with … 

MICHAEL CHE A financial bonus? No, it doesn’t.

Well, that’s a shame.

COLIN JOST Yeah, so if you know any agents looking for clients. 

Is there added pressure?

CHE I bet there’s some level of that for Lorne and the producers. For us, we’re just trying to find the fastball funny thing, that’s what keeps you up at night. I try not to think about it in the macro — in season 51, we can look back at 50 and say what was special about it, but it’s impossible to determine what is going to be special. You can’t plan for a perfect moment.

JOST Yeah, there could be something that happens between now and the 50th — hopefully something happens.

CHE Like, what was it, five summers ago when they shot at Trump at a rally?

OK, in moments like that …

JOST What did you do with the gun? 

That was not my question! In moments like that, do you think, “I wish we were on the air”? Perhaps it’s not your first thought, but is it your second or third?

CHE In that moment, I was like, “Thank God that bullet missed or we’d be in a civil war.” Then I was like, “Oh, his poor beautiful ear,” that was the second thing.

And the third? 

CHE Sometimes it’s a gift and a curse to have that sort of thing to make fun of because, as a comedian, your mind immediately goes to being funny. But also, a former president was just shot at and this might not be the time to make a joke about it for the half of the country that is really sensitive about it. Of course, Trump’s so crazy, a week later, nobody cared.

JOST I had to do a show that night at this event where there were a bunch of comedians, and everyone was like, “You still going to do a show?” It was like two hours after it happened, and it’s such a charged thing and you don’t want to go into it and be disrespectful, but then people are expecting something on it and they’re sort of disappointed [if you don’t deliver]. 

So, what did you do?

JOST I don’t think I really talked about it or maybe I mentioned it, but I got away from it quickly because I didn’t feel comfortable joking about it yet.

Does the prospect of another election season excite or exhaust you?

LORNE MICHAELS I think there’s two things happening at the same time at SNL: an election — and I’m tired of everybody telling us it’s the most consequential one in history because there’ve been a lot of big elections — and the 50th anniversary. And I want to celebrate this season with people coming back who’ve been part of the show and who love the show — not so much as hosts but just making appearances, and so the election is a chance for that because that’s five or six shows. So, Maya and some others coming back for the election will be fun for everybody. And, at the same time, there will be new people emerging, a different generation.

CHE For us, on a comedy level, it’s hard to tell until you’re there. It’s like in boxing: You really don’t know until you get hit in the face the first time. It’s usually just about having something to say, and that’s what makes it fun and stressful — trying to articulate it and get it on time and before all the other comedy shows do it.

Well, the beauty of Trump is that he’ll keep giving you new material.

CHE It’s also the ugly of him. I remember one time I did a show at Comic-Con …

JOST Brag! 

CHE Sorry, no, it was SantaCon, excuse me.

JOST OK, maybe not a brag. Are you OK? 

CHE I was at a dive bar on 14th Street with all these Santas, and this one guy was dressed as a giant penis with a Santa hat and he sat right in the front and he was blackout drunk and heckling. It was the first and only time I’ve asked security to remove a customer. But I was like, “You’re wearing the insult, I can’t compete with that and I don’t want to.” To me, that’s the level of covering Trump. You’re like, “He said what? Alright, get out of here, you’re just asking to be made fun of.”

In this metaphor, Trump is the penis Santa, correct?

JOST Yeah, it’s one for one.

CHE Yes, he’s a dick, but people think he’s going to bring them gifts, so they love him. 

Photographed by Gavin Bond

At this point, with only weeks to go, how are you preparing?

CHE I don’t even think about that stuff until we’re about to do the show because it changes so fast and it has for the past eight years. 

JOST The weird thing now is as soon as news like Kamala’s running happens, America just starts debating who’s going to play them on SNL. Before we’ve even had a conversation about it, there’s a list of 10 people who should play Tim Walz.

CHE (To Jost) You kind of started that by having Melissa [McCarthy] play [Sean] Spicer, no? I feel like that wasn’t a thing when I first came here and it became a thing.

I suspect having non-castmembers come in to play politicians doesn’t always sit well with those in the actual cast. Am I right?

JOST If you’re someone in the cast who’s like, “I have a better impression than that person coming in,” it’s probably frustrating. But it’s sort of the reality of our show. 

Photographed by Gavin Bond

Will James Austin Johnson continue playing Trump or do you welcome Alec Baldwin back?

MICHAELS I think James will be there, but I don’t want to get into what I’m doing.

So, you’re not going to tell me who you’ve got playing J.D. Vance?

MICHAELS No, but I think we have the people to play [the candidates] and it should be fun. And Trump has morphed. James, who I think is brilliant, played Trump as the sort of diminished Trump. The guy at the back of the hardware store holding court, and that played because it felt relevant. But we are going to have to reinvent it again because, well, you saw the debate. One of the great parts of show business is that you can’t come back with the same show. So, all of these characters have to be reexamined, and if it makes sense and feels relevant, you know you’re on the right track. But if it feels like you’re talking to the audience and want to be supported because your values are the same as their values, you really shouldn’t be in comedy. 

Steve Martin said you’d reached out about him playing Tim Walz, and, as he told The Los Angeles Times, “I wanted to say no, and by the way, [Lorne] wanted me to say no.” Is that last part true?

Yeah. Steve and I have been very good friends for longer than you’ve been alive, and it’s not the thing he does. But there’s lots that he does that you’ll be seeing.

I’ve heard you say that Republicans are easier for the show than Democrats, in that Democrats tend to take it more personally. Is that still the case? 

MICHAELS Yes. And it’s not personal in the sense of an attack, it’s just, you did say that and you did do that, so were you thinking it would be rude for us to comment on it? That’s what we do, and we’re going to do it again.

Political parodies over the years have included Melissa McCarthy as Sean Spicer, Kate McKinnon as Hillary Clinton, Chevy Chase as Gerald Ford, Maya Rudolph as Kamala Harris, Will Ferrell as George W. Bush, Alec Baldwin as Donald Trump and Dana Carvey as George H.W. Bush.

Dana Edelson/NBCU Photo Bank/NBCUniversal/Getty Images (3); Will Heath/NBC/NBCU Photo Bank/Getty Images (2); Al Levine/NBC/NBCU Photo Bank/Getty Images; Alan Singer/NBCU Photo Bank/Getty Images

In the past, you’ve also said that whoever is in power, the show is against them. Has that remained the case in recent years? Bowen Yang, for instance, was vocal when Nikki Haley stopped by the show — and on the night that Trump won in 2016, it almost sounded like you were presiding over a funeral backstage. 

MICHAELS Yeah, no, I think there’s less of that happening now. I think that people began to believe that their authentic self was who they were online and so they had to stay true to their beliefs, which is a great thing to do, it really is. And it also presupposes that your beliefs will never change. Our job is, you’re playing that guy, and whoever that villain is, you have to find a way to make it entertainment. You can’t lecture the audience, which most of politics is now, people lecturing the audience. Ours is like, yeah, there are kind of idiots on both sides. And we’re not going to do anything that didn’t work at dress [rehearsal]. It has to play. It has to be comedy. We’re first and foremost a comedy show. 

Michael, I’m curious if it still feels like the show speaks truth to power? You did an “Update” joke last season about Biden struggling to connect with Black voters, and the audience seemed horrified.  

CHE It’s hard to answer because I think as the writing staff grows and as the cast grows, SNL is like an apartment building, not a house. So, we all live together, but we don’t really live together. A cold open could go down and I’ll be like, “I don’t like this one bit,” but it’s not my voice and it’s not up to me. I can’t agree with everything political that we’ve had on the show. And I’m sure there’s stuff I’ve written that’s made some castmembers bristle or some writers go, “What are we putting on? We can’t say that.” But we have to live with each other; we’re renting this space and trying to get this real estate for our ideas. So, there’s no one mission statement, I don’t believe, beyond funny is funny. Maybe Lorne has an idea of what he wants the identity to be. 

Now, there was a certain time in the past eight years or so where the country became way more divided and the people who do sketch comedy leaned on a certain side of the fence. But I agree with Lorne — the show is not about being left leaning or right leaning or any leaning. It’s about seeing the truth and pointing out that the emperor is not wearing clothes. That’s what I like about comedy, so I’ll always go for those types of jokes.

So, what did you make of how your Biden joke landed?

CHE I always say, as corny as it sounds, at SNL, we’re not the A students, we’re the kids in the back of the class throwing spitballs at the teacher. But I think the audience might feel like comedy is going to tell them the truth because they don’t trust politicians anymore, they don’t trust news even, and so they’re very protective of it and they feel like if you say something against a side, it’s almost traitorism. It’s almost treasonous to make fun of Biden or the left when Trump is running, and I get that feeling, but as time goes by and we face more disasters and crisis, we’ll understand that this was all a ridiculous time.

In terms of hiring, what were the needs this season?

MICHAELS With the pandemic, there was no letting anybody go since there was no place to go. So, we just kept adding people because you have to do that to renew the show. But most people weren’t getting on enough because it was way too many people to take care of and you only get better by doing it all the time. And when people weren’t getting on, you had this frustration. Also, a lot of the places like Second City and UCB and Groundlings closed down [during the pandemic], so there was a whole generation that didn’t get to come and audition. Stand-ups did. And then there were the strikes. So, this was the first time in a while where I could just look at the show and go, “This is what’s happening” — and we just had to make changes, so we did and we’re excited about the new people because they’re people we felt really belonged at SNL.

How much more concerned are you about being politically correct today versus when you started? 

MICHAELS We had a bad time when I added Shane Gillis to the cast [in 2019]. He got beat up for things that he’d done years earlier [racist and homophobic jokes] and the overreaction to it was so stunning — and the velocity of it was 200 Asian companies were going to boycott the show. It became a scandal and I go, “No, no, he’s just starting and he’s really funny and you don’t know how we’re going to use him.” And when he came back to the show last year [to host], we saw, “Oh right, he’s really talented, and he would’ve been really good for us.” Now, his life turned out well without SNL, but my point with it is everything became way too serious. It was like a mania. And the velocity of cancellation — and lots of people deserved to not be liked — it just became not quite the Reign of Terror, but it was like you’re judging everybody on every position they have on every issue as opposed to, “Are they any good at the thing they do?” I do think that period is winding down and, I believe, the people who do awful things will still be punished.

“I’m the last person standing who thinks network TV is important,” declares Lorne Michaels, seated in SNL’s famed Studio 8H in New York City.

Mary Ellen Matthews/NBC

Will Ferrell and Harper Steele have been doing press for their new doc [about a road trip the former SNL collaborators took after Steele transitioned to a woman].

MICHAELS I loved it.

Will is now saying that he regrets playing Janet Reno; while Harper noted, on the subject of men playing female characters: “I’m purple-hair woke, but I wonder if sometimes we take away the joy of playing when we take away some of the range that performers, especially comedy performers, can do.” Curious where you fall and what you make of the debate?

MICHAELS My feeling always is trust the audience. We do a dress rehearsal, and you can tell when something just has a bad feeling to it. It gets the laugh, but it’s the wrong kind, and generally it stops there. But I saw that they were discussing Will playing Janet Reno, and there was a sweetness to it. We liked his Janet Reno. So, I understand why it’s inappropriate now, but somebody has to speak up to the inappropriate, and that generally is us.

Is there a host you wish you’d snagged but never did? A white whale, if you will.

MICHAELS We tried very hard for Clint [Eastwood], particularly in the seventies. Movie stars in that period did not do television. Occasionally they did with us, but there was a real chance of being humiliated in front of millions of people and we don’t pay anything, so you’d have to do it because you were game for it. In the end, pretty much everyone has [come on], so there’s no one out there where I go, “Oh, if that person would just do it, my life would be complete.”

CHE I’m fortunate enough to have had a lot of white whales come through — Sandler, Murphy, Chappelle. My white whale at this point would be Denzel Washington. He’s kind of our Brando, and it would be amazing to just see him be silly and funny.

SNL’s “Weekend Update” anchors Colin Jost (as Kamala Harris) and Michael Che (as Donald Trump) were photographed Sept. 10 at PMC Studios in New York.

Photographed by Gavin Bond

There’s been so much attention paid to Lorne’s retirement plans in recent years, though looking back it seems he’s the one who first started the post-50th rumors.  

JOST Of course. It’s almost like he had a plan. 

In 2020, he said he deserved to wander off after the 50th. So, what do you think changed?

JOST Well, I think he said that anticipating that end goal, the same way by the end of a season we’re all like, “We’re going to take the summer and disappear and not do anything and not talk to anyone and maybe not come back,” and then the summer passes and you’re like, “Oh yeah, it’s fun.” I think he thought of the 50th that way, too. At that time, it was three or four years away and he was like, “After that, I don’t want to do it anymore.” Then, as it’s getting closer, I think he’s realizing that he loves doing it and I’m not surprised at all that he’s now like, “I’ll stay.” I always thought that was just him strategically announcing it and having that end goal, but never necessarily intending to [leave] then because it’s what he loves doing.

Lorne, what changed?

MICHAELS I think the times, and also there are not many network shows left, and this one has taken on [an importance]. It’s more about keeping it on course than anything else, and, obviously, I really love it. And every year there are more and more people that I rely on for other things, but, in the end, you really need someone to say, “This is what we’re doing.” So, I don’t really have an answer; I just know that this is kind of what I do and as long as I can keep doing it, I’ll keep doing it. There’s no immediate plan.

The show’s original cast in 1975 included (clockwise from left) Chevy Chase, John Belushi, Gilda Radner, Garrett Morris, Dan Aykroyd, Jane Curtin and Laraine Newman.

TV Guide/NBC/Courtesy Everett Collection

Internally, it must have prompted conversations about succession. What have those entailed?

JOST You’d think there was a lot of speculation about it internally, but there really isn’t because no one who works there thinks he’s leaving. Everyone is busy figuring out whatever the bigger problem there is that week. I think everyone thinks we plan way more ahead than we do. But you do have to deal with all the speculation [from the outside] and everybody asking you, “Who’s it going to be?” 

CHE Maybe a lot of it has to do with being a child of divorce, but I don’t want to think about Lorne leaving. I mean, really, nobody wants to face the reality that, at some point, he won’t be doing it. 

JOST And all the people that are being talked about as possible successors, no one wants him to leave and no one wants to have to follow him.

CHE Honestly, I don’t think it could ever be done by one person again. I think it will be a full committee. The show is in his image. I think people will appreciate when it’s not around anymore how much he actually has done for comedy. Any other show loses a star like Will Ferrell, and the show is not the same. SNL has lost maybe 30 of the biggest comedy stars of all time, and it’s still on and relevant. 

JOST It’s actually humiliating for Will Ferrell.

CHE Yeah, he should have left a bigger mark. (Laughs.) But it’s a testament to how great Lorne is at the show and how special the show is to people. Just the interest in who’s doing it next shows how important it still is to people. I mean, people get mad at us for who we let host. It’s like a right to be able to host, like they’re running for Congress or something.

If you see on your phone that Lorne’s calling, what’s your immediate reaction?

CHE Something’s wrong. I’m always like, “Uh oh, who did it and how are we going to fix it?” Or it’s something like, “Oh no, we’re hosting the Emmys.” But I have a great relationship with Lorne. I think everybody’s relationship with him boils down to the fact that he’s one of the few people who you truly respect their opinion about show business because he’s seen it all. Groundhog Day is one of the greatest movies ever because it’s the perfect story of comedy where you do it all the time and so it’s new to everybody but you. You just slowly get better and better and before people know it, they’re like, “How did you learn how to play piano?” “Well, I’ve been doing it every day in every town.” Lorne is sort of that with careers. He’s made so many stars. So, I don’t even like to think about him not doing it anymore. Colin’s going to cry.

Colin, his name pops up on your phone, what’s your first reaction?

JOST It depends on what time it is and what section of the year it is.

CHE If it’s 3 a.m. and it says image, FaceTime video, boss has been drinking. (Laughter.)

JOST No, but he’s such a night owl and he has different relationships because of it. He’s up till 3, 4 a.m. every night, so he has certain people he knows are always up then too, and they’ll have communication between the hours of 2 and 4, and not in like an “out drinking” way — just a regular noon conversation but it’s 3 a.m.

Are either of you those people? 

CHE I definitely am. 

JOST I had a long run, but I can’t be anymore. I think he’s learned that I’m not going to respond until 9 a.m. and then he’s going to see it at 11 a.m. when he wakes up.

Colin, Michael, you’ve both flirted with the prospect of leaving the show yourselves. Colin, you wrote about leaving in your book …

CHE (To Jost) When’s your book coming out? [Jost’s memoir, A Very Punchable Face, was published in July 2020.]

JOST I’ll send you another copy.

What is your current relationship to the show?

CHE I think “Update’s” good, but the only reason I think that is because people are willing to tell me it was bad. You only know you’re doing OK when people tell you that you used to be terrible. 

MICHAELS Six or seven years ago, somebody high up at the network who never asked me SNL questions out of respect said, “ ‘Update’ with Jost and Che, do you think that’s working?” And I said, “No, not yet.” And he said, “Oh, you know.” I’m like, “Of course I know, but there’s a chemistry there.” And we’ve had lots of good combinations, but these two just brought out the best in each other. Like, who else could make jokes about Colin and Scarlett [Johansson, Jost’s wife]? And the joke swap? Whatever hostility you thought was lurking below the surface, that is all visible in the joke swap, but it’s meant to be funny and it’s truly funny. I just like that Che can take these positions, which kind of fly in the face of the values of most of the audience, and he’s funny and they laugh and they like him.

The “Weekend Update” desk has been occupied by Amy Poehler and Seth Meyers (top left), Jane Curtin and Dan Aykroyd (pictured with Michaels), Norm Macdonald (bottom left) and current anchors Jost and Che.

Al Levine/NBCU Photo Bank/NBCUniversal/Getty Images; Will Heath/NBC; NBCU Photo Bank/NBCUniversal/Getty Images; Dana Edelson/NBCU Photo Bank/NBCUniversal/Getty Images

When it comes to the joke swap, what are the ground rules? As in, where is the line?

CHE I don’t know that there is a line. I think anything can work given the circumstance, and also nothing can work given the circumstance. So, my thing with joke swap, which is the most stand-up thing that we do at SNL, is that the audience just has to believe that I’m trying to embarrass Colin and that this really bothers him and vice versa. And if that comes across, they’re not thinking about the content of the joke. So, it’s not, “Oh, that’s a racist joke,” it’s more, “Oh, I can’t believe he’s going to make him say that out loud.”

Do you ever get nervous about pushing too far? 

CHE No. And I feel bad that it’s no, because maybe it shouldn’t be no. And there’s stuff I’ll want to try and they’re like, “You can’t do that,” and they may be right, they may be saving my career, but in my head, that’s why the show is live. Some stuff can’t work so that when stuff does, it feels like magic. 

Why do you think you’ve both ultimately stayed at the show?

CHE My mortgage! No, we love it. We love the show. And it’s a weird thing because you get moments where you love it so much that it drives you crazy and you want to be as far away from it as possible. 

JOST It’s like when you play golf, a lot of times it’s very frustrating and there are times where you certainly consider quitting, but then you hit a good shot and you’re like, “Whoa, I love this game. I should do this all the time.” And that’s the way it is with SNL. When everything comes together and all the costumes look great and the timing is perfect and the crowd’s good, you’re just like, “This is the best job in the world.” 

CHE And we’ve been doing it so long that it just becomes part of what you do. I mean, it consumes so much of your thought process, you start thinking in jokes and dreaming in jokes.

JOST The nice thing about the beginning of every year, like the beginning of a school year, is you don’t know exactly what it’s going to feel like and it’s probably going to be different than the other ones. So that’s always exciting, at least for a little while. 

MICHAELS Everybody in the off-season speaks so fondly of the job and then they get back into it and go, “Oh my God.”

So, will you be here at this time next year?

JOST I’m going to be living in this room either way at that point.

CHE I try not to think about it because then I think it ruins the morale for the rest of the year. I just, I don’t know, you never know. Hopefully I say something and I don’t make it through the year. 

What could you say at this point?  

CHE Oh, that sounds like a dare. 

Looking ahead, what else do you want to do?

CHE I just want to have fun in my career.

Have you not been having fun?

CHE I think sometimes I don’t. I’ve got to consciously remind myself that this shit is finite and to take advantage of the doors while they’re open and try to do some fun stuff with your friends and people that you truly believe are funny as long as you can. Because you could go on the road and make millions of millions as a stand-up and it’s a lonely life. 

JOST And one thing Lorne always says is, it’s so hard to make something, let alone for it to be a hit. Perhaps he says it to manipulate us to stay, but I also think there’s truth to it.

CHE For me, I just want to do fun projects and be able to pay my mother’s mortgage. As soon as that mortgage is paid, I’m getting that rope and three-legged chair. 

JOST That’s a great ending.

CHE Che was here.

This story appeared in the Sept. 19 issue of The Hollywood Reporter magazine. Click here to subscribe.