Late-Night Laughs: Lilly Singh Breaks Free Of The “Creative Crutch” Of The Desk & Looks Ahead

Lilly Singh

Lilly Singh launched the second season of her late-night show A Little Late in January – having been off the air for nearly eight months due to the pandemic.

She returned not in a studio as she was in season one, but in a house in Los Angeles, that made the NBC show feel more casual and also allowed her and her team more easily able to film during Covid-19.

Singh tells Deadline how they achieved that, how breaking out of from the behind the desk was the best decision for the show and how she’s feeling about doing more of the show after season two ends.

This comes as the YouTube star gets ready for Boss Week – a week of shows, starting March 22, where she will interview powerful women that generally don’t appear on late-night shows including Melinda Gates, Ayesha Curry, Whitney Wolfe Herd and Renee Montgomery.

DEADLINE: Congrats on making a show during a pandemic. How are you feeling about it?

Lilly Singh

LILLY SINGH: I’m super pleased and proud. I’m impressed with humans’ ability to adapt, particularly in our business. We’re taking all of the protocols and using them to try and make a show.

DEADLINE: What promoted the decision to move out of the studio and into the house?

SINGH: It’s a happy result of what we were forced to do. I was very big on saying ‘This is the circumstances that we have to shoot in, how can we make this to our advantage and beneficial to us. We took the creative by the reins and saying ‘This is the vision I have and this is the vibe that I want and making decisions to make that happen. I feel a lot more comfortable and happier and I’ve really put myself in a position to create what I think is good for the show.

DEADLINE: You stepped out from the behind the desk, which is a late-night institution.

SINGH: I never really felt completely comfortable behind the desk or in the studio. For me and for what my vision was, I felt it was very limiting and it wasn’t a lot of fun and I wanted to go the more inviting and warm casual route especially because my show is on at 1:30am and because of who I am as a person. The house was a perfect choice for me and in addition to even removing the desk, it’s the format of the show that I’ve built, which is you get a behind the scenes look at what it takes to make a late-night show and that’s a story that we don’t always get told. We watch late-night shows and we know what to expect. I want to create a show that has a nice storytelling element.

If I’m really honest, I was using the desk as a creative crutch and I said ‘I no longer want to use that crutch’, I’m breaking this and so now I am a lot more free to get up and move around and truly break the format. That was a very active decision.

DEADLINE: You’re halfway through this season with 40 shows. That seems like it’s gone very quickly.

SINGH: Every day I can’t believe I’m halfway through. Genuinely, me and the crew are having a lot of fun, we’re happy with the changes, the interviews are right on the mark where we should be and time is flying because we’re all having a blast. I had a few goals going into thisS eason and one of them was the way we break the format, to show the magical behind the scenes moments and a lot of them are not scripted. I improv a lot. We have a super tight crew and a very small footprint, by force, because we shoot in a house so the room that allows the most amount of people is seven people. Going into this, I ensured that turns to our benefit. At first glance, you might think a crew of seven people is tough but that resulted in me improving a lot more because there aren’t the writers right there. There are less people around slowing down the process in some ways. Everything is so tightened before we shoot, I can improv and everyone steps up and does their job so there’s a beautiful silver lining of efficiency that comes from that.

One of the things I’m most happy about this season is the inclusion of more sketch. I love doing sketch, writing sketch and performing sketch. I’ve been writing a lot more and unlike the previous season a lot of the sketch ideas are mine, I’m in every pitch meeting and I am brainstorming with the writers. We have the sketches but once I’m that character, I’ll do a take where we just play. And because I’m usually every person, I can play.

I also like making commentary that’s straight to camera, which are the rants, which have replaced traditional monologues, I think there’s a time and place for that. For instance, recently I did a rant about the Proud Boys becoming a terrorist group.

DEADLINE: That rant, which came out in February, seems very timely given the recent murders in Atlanta.

SINGH: I actually just sent an email to my head of digital to clip a section of the Proud Boys rant and post it on social because I think it speaks to exactly what’s happened [this week]. I don’t think this is an area that’s new, I think it’s been around a very long time and is something that people of color have had to deal with for a very long time, which is why that Proud Boys rant is so important. For so long, people understand that online they’re called one thing, that we understand, but I want us to go deeper. What is the consequence of doing that. I don’t want to do a rant where I say I’m sick of people of color being called terrorists. You see that all the time. What I want to do is find out what is the consequence. I’ll connect the dots for you. There’s a moment where you just think it’s an idiot on Twitter but you don’t always go through the motions to say ‘Where will this lead us’ and it leads us actually having these ideologies and then people being crazy enough to act on them.

That commentary is so pointed in a rant but I’m also a big fan of commentary that’s relatable and that happens in sketch. I do a sketch called Kamala Harris Is Black and Indian, Period. That has a lot of commentary but it’s through sketch where people can laugh. Kamala Harris becoming Vice President was music to my ears. A person I can look like for real.

DEADLINE: You changed up your team this season with Neil Punsalan taking over as showrunner and Chelsea Davison becoming head writer. How’s that working out?

SINGH: It has worked out how I envisioned it. One of the smartest things you can do as a creator is empower yourself by putting a great team in place and I feel like I have really succeeded in doing that. Everyone on the crew does support the vision I have. The writers’ room is full of people who know how to capture my voice and point of view and when you’re someone like me who has such a unique point of view that is different from the rest of the late-night space, it’s important to have a writers’ room that understands that point of view. I’m really happy with the team.

One of the most important things is for them to be able to capture my voice but it’s also can they fill in the gaps. I do a lot of sketch and they offer me something that isn’t second nature to me. I like working with people, particularly writers that have experience and people that don’t. I know when I first started the show, there was a lot of pressure to have people with experience. But there is an advantage to have people that don’t know things are traditionally done so they’re not married to a certain way of doing things. My show is not a traditional show, we do things differently across the board so for me, it’s beneficial is someone comes in and has no preconceived notions of how this is supposed to work. For a lot of my writers, this is their first writers’ room and a lot of people would say that’s a risk and that shouldn’t happen for a show like this and I disagree. My writers are crushing it and I believe that’s because they don’t have all of these ideas of how they should structure things to look like and how long things should be. I’m breaking all of those rules so they better break them too.

On day one, I told my writers ‘When you pitch me an idea, pitch it to me with the YouTube video title that’s going to work with it and unless you can do that, it’s not going to work. That’s a way of thinking that I don’t think you would learn anywhere else and it’s because of that digital savvy.

DEADLINE: The show goes out at 1:30am. Are you still happy with that time slot?

SINGH: I am still happy. Going in to this, I’m trying to make things my advantage so of course you can go into the show and think it’s on at 1:30am so we have to shoot things a certain way. No. It’s going to be consumed online. It’s going to be consumed the next day. Let’s use this to our advantage. We can shoot things in a way that they don’t have to be live to tape. In season one, one of my biggest hurdles was shooting live to tape and it was always very tough for me and this season I said I wasn’t going to do that and our schedule allows us not to shoot live to tape. We always considered that a disadvantage, but let’s flip the script and make interviews 45 minutes long and cut them down. We are shooting and then extracting the best in post so that those clips and tight, concise and strong.

DEADLINE: Since the show premiered initially, NBCUniversal launched Peacock. Did you ever have conversations about putting the show on there a little earlier in the evening?

SINGH: I have not had those conversations, to be honest. I try and not get too in the weeds on all of those things because I’m so in the weeds on the digital space. I am much more particular about how it’s executed online.

DEADLINE: Similarly, since you debuted, you’ve been joined in late-night by Amber Ruffin, Desus & Mero’s show is doing well and Sam Jay and Ziwe are coming soon. It seems late-night is becoming a little more diverse.

SINGH: I agree. All progress is good progress. I would love nothing more than to see more women, more people of color in these positions because I think it’s exactly what we need.

DEADLINE: You’re launching Boss Week with guests such as Melinda Gates and Ayesha Curry. What’s the idea behind that?

SINGH: It’s very fun to talk to famous people and A-list celebrities and I love that but I also had a strong desire to have deep conversations with people who aren’t always on read carpets but they have so much to offer and Boss Week is my tribute to boss women who are killing it in whatever industry they’re in and my opportunity to dive into their brain and swim through their thoughts.

DEADLINE: Given you’re halfway through season two, have you started to think ahead. Have you spoken to NBC about a third season?

SINGH: I am just trying to make it through this season and make it through the Covid. I’m loving and enjoying this season and I feel more comfortable than season one. If you asked me this question at the end of season one, my answer would have been ‘I have lots of grey hair’ but this season, I’m thoroughly enjoying so if I get to keep having deep conversations with people and keep creating, I’d love to do it. I’ve learned you can’t do it if you don’t enjoy doing it because of how all-encompassing it is. A daily show consumes your life and there’s no way to get around that.

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