When it comes to live music gigs on television, few slots are more prestigious than Saturday Night Live. If you play SNL, there’s a sense that not only have you made it, but you’re an artist the world will be seeing a lot more of for years to come.

The venerable comedy institution celebrates its 50th anniversary this year, which you’d have to be living under a (30) rock to miss: In addition to two excellent documentaries, Ladies & Gentlemen… 50 Years of SNL Music (directed by Questlove, no less) and SNL50: Beyond Saturday Night, this holiday weekend sees two massive celebrations of the show’s impact take place in Manhattan and on screens across the country. On Friday (Feb. 14), a cavalcade of musical stars hit the stage at Radio City Music Hall for SNL50: The Homecoming Concert (streaming on Peacock) and on Sunday (Feb. 16), SNL50: The Anniversary Special airs. (On Saturday, NBC re-airs the first-ever episode of the series, which featured Janis Ian and Billy Preston as musical guests.)

In the midst of the madness, two people who help Saturday Night Live book its musical talent gamely hopped on a Zoom call with Billboard to discuss how they go about bringing singers, rappers and bands to the SNL soundstage. Talent producer Rebecca Schwartz has been at SNL in some capacity since 2015 (MGK was the first artist she picked up the phone and offered an SNL slot to), while coordinating producer Brian Siedlecki began as an intern back in 1996 (the first artist he booked was Nelly Furtado when “I’m Like a Bird” hit).

The interview has been lightly edited for length and clarity.

What’s a typical week for you like?

Rebecca Schwartz: It changes tremendously based on who the musical guest is, but generally, they won’t walk into the building until Thursday. So Monday through Wednesday we are having production meetings with their creative team. We’re having calls — hopefully, this is taking place before the week of show, but oftentimes, is very much happening the week of the show – and fine-tuning their sets and [talking about] the parameters of what’s actually capable of being built in the very, very small music set. Then we also are simultaneously having labels come here or going to label’s offices. We’re taking incoming pitches all the time as well.

Brian Siedlecki: And going to see people perform concerts, showcases, festivals. We’re paying attention to things like TikTok and streaming. We’re listening to pitches but we’re also aggressively pursuing artists that we believe in and seeing if there’s any flexibility in their touring schedule to make them available in New York for three days.

SNL is such a prestigious gig for any artist. I would imagine you have an embarrassment of options to choose from each season.

Siedlecki: Sometimes. But with people’s touring schedules, it makes it really difficult. They don’t come in for one day like some of these other [TV] shows. And it’s super expensive to do our show. So they want to perform on our show when it makes sense for them. There’s wardrobe, they’re keeping their crew in New York from Wednesday to Sunday, they might bring in lighting. It all adds up pretty quickly.

Schwartz: There usually has to be a label somewhat involved in financing the appearance. There are so many moving targets. When I first came here, and this is with hosts as well, I had a little bit of, “What’s so hard about this? Who’s the most famous, exciting person right now? Of course they’ll want to do SNL.” Which is true. However, there are so many variables. Sometimes people truly don’t have two days off in a row. Sometimes people aren’t in an album cycle and they really do have this incredible performance, but it costs half a million dollars and they don’t want to pay out of pocket for that. It takes a lot of scheduling, which is not sexy.

Scheduling is half the music biz. Obviously booking Paul McCartney is an easy yes, but what makes an up-and-coming artist SNL worthy in your opinion?

Siedlecki: Sometimes it’s clear as day, like Olivia Rodrigo and how quickly she exploded. Chappell Roan, same thing, it’s just trying to figure out when’s the moment. By the time we had her on she was a huge star. But then sometimes it’s just like, Rebecca booked Mk.gee and saw his live show and was totally wowed by him. It was a really cool live performance and we fought to get him on.

Schwartz: At the end of the day, Lorne [Michaels] really does make every decision and have an opinion on it and is involved. If it’s somebody where he’s not seen any media on them, we put stuff in front of him and he has input on these things. Mk.gee, we obviously loved the music, and [he is popular] amongst certain cool-music-guy crowds. [We saw his show and] it just it felt like nothing either of us had seen before. Because we have so many incredibly famous, accomplished artists, there aren’t that many slots necessarily for people who really are like, “This is a freaky risk, but we swear it’s [worth booking].”

Siedlecki: Throughout the season, we are able to take chances. We’ll book newer artists where the general public might not know them by name, but they know the song. And then there’ll be some artists that we book that people are like, “Wait, who is that?” A lot of times it’s just trusting our gut and who gets us excited. Everyone in the office clues us in on people they’ve heard or seen or are excited about. So it’s definitely an open conversation about who we’re going to book.

Do cast members stump for their favorite artists?

Schwartz: All the time. Which is amazing. That’s what makes this show varied and prescient. There’s a very broad spectrum of tastes and metrics and ages, we actually do have a pretty diverse office in every definition of that word. Everybody is very much encouraged to see stuff and report on it. We do try to take in as much information as possible, even stuff that’s not our sensibility. Lorne is very good at that too — stuff that isn’t necessarily his sensibility, but he understands its value to people.

Siedlecki: At the end of the day, we just want an amazing performance whether or not it’s our type of music.

Do you ever get someone pitching you on a concept and the staging just doesn’t work, and you have to pivot last minute?

Siedlecki: Occasionally. We will know what will work and what won’t. If an artist is super passionate, we’ll say, “OK, let’s try to accomplish it and take a look at it on Thursday.” But we’ll really encourage them to have a backup plan. Most of them are pretty agreeable to it.

Schwartz: We are always encouraging people to take big swings and I do think we are a very artist-friendly show in that way. We are not precious about the sets; we want it to look how the artist wants it to look. With that said, there are very real physical restraints. We will always try anything somebody wants, but it’s like, “Let’s be realistic. You should absolutely have a contingency plan for when, like, your harness doesn’t lift you up.”

Siedlecki: We include our lighting director, our director, our set designer in all these conversations. They may have ideas that they think will help accomplish the look that [the artist] wants without necessarily doing exactly what they want just because of the parameters of the studio. It’s very much a collaborative process. The hope is that by Thursday, they come in and they don’t have to worry about the set. It looks great, we do minor tweaks, and then they can just worry about the performance.

How does it work with having artists in sketches?

Siedlecki: We try to gauge interest at the beginning of the week, just to make sure we’re not wasting anybody’s time. We’re very involved in that.

Schwartz: Especially if there is someone that is really excited about wanting to be a part of it, we will campaign a little bit for them as well, just to make sure the writers are aware that this person is around and available and interested. And try to get them to be used.

Siedlecki: And during read through, one of us might have an idea of like, “Oh my god, we should get Billie Eilish to play this character or do this impersonation.”

What are you doing during the actual show?

Siedlecki: We get notes from Lorne after dress rehearsal, and some things we have to address. But in most cases, by Saturday night, things are pretty much tweaked and ready to go.

Schwartz: There certainly have been scenarios where after dress, something is truly not functional. On Thursday, during camera blocking, we try to give Lorne a heads-up if there’s something [amiss], like if we’re having lighting disagreements with their in-house creative. So we try to flag that stuff so even if we don’t have a contingency plan on Saturday, we can limit the contentiousness when we ultimately do have to go to them. Sometimes we will have it queued up on a laptop so we can watch back the dress rehearsal and go like, “You can see that the strobing is crazy,” or whatever. Generally, we all agree. Those are rarer than often, and we hope to not have to do any tremendous recalibrating between dress and air.

Siedlecki: Some of these artists and creative people are so used to creating for a tour or something like that, and so they come into our studio and it’s a very different environment. So we do have to tame down some of the smoke or some of the lights. It’s tricky to figure out for TV. It’s a big look for these artists. I think they’re like, “This is my one opportunity. I want to blow it out of the water.” And so they try to do that in every way.

This weekend you have two big SNL events.

Schwartz: Friday [is happening] basically because of the fact that on the Sunday show we can’t have as many musical artists that have been impactful [on SNL] for over 50 years. The documentary was stunning, and that was a fraction of the artists. Friday is sort of functioning as our best attempt at covering genres and time periods. And then Sunday will be a micro-version of that as well, of different genres and age groups and people that have a connection with the show.

There have been over a thousand performances on SNL over the years. I actually had this crazy idea of watching all of them and ranking them, which I quickly abandoned.

Schwartz: Questlove did that, by the way! He didn’t rank them, but he watched them in preparation for the documentary. He really has an encyclopedic knowledge of every performance and if dress was better than air, which sometimes it is. I think he did that for about a year.

He absolutely is an encyclopedia of music, that doesn’t surprise me. Do either of you have a favorite musical performance, either during your time on SNL or before? Whose performance hit you the hardest?

Schwartz: Well, that’s Lana Del Rey. I love Lana.

Siedlecki: That hit me the most in different ways. [Laughs]

Schwartz: He worked [on that one], so it was different. But as a fan and person who was not employed [here], I just remember seeing that performance in real time being like, “This is fully Warhol performance art, it’s so cool. Can’t believe this is on SNL.” Obviously, the next day I was truly surprised by other people’s experience of it, but I do remember watching that as a fan and being like, “This is exactly what she does.” It’s incredible that they gave her the platform to do that because she is an artist.

I think she’s been vindicated in the long run. But yes, at the time, people were hard on her.

Siedlecki: It was tough, it was stressful. But she is someone we believed in. That album was incredible, and we stood behind it. We still do. For me, when Prince came through, I was like, “Is he really showing up?” And then it was incredible to be there and talk to him for three minutes. Just, wow.

Schwartz: I had just started and obviously I didn’t speak a word to him or even be in his eye line, but I watched from afar. I don’t know if I saw his feet touch the ground. He floated. He really was as mystical as you would have hoped for.