Longtime creator Lilly Singh has done her fair share of trailblazing. The millennial Canadian multi-hyphenate rose to internet fame in the first generation of YouTube stars, then became the first YouTuber to make the jump to network television — as well as the first woman, let alone the first young openly queer woman of color, to host a late-night talk show there. This month, the 34-year-old author, comedian, actress, filmmaker, and television host made her debut as one of the leads in the new Muppets show on Disney+.
For the latest episode of On With Kara Swisher, Swisher spoke with Singh about the Hollywood hustle; the difference between making content for YouTube, Instagram, and TikTok; and bridging the still-sizable gap between dynamic social media and old-school linear television. In the two segments below, Swisher and Singh discuss what old media still needs to learn from new media, why the Met Gala needs more internet stars, and how Singh has come to terms with what her success can and can’t be for the overlapping communities she represents.
On With Kara Swisher
Kara Swisher: So talk about the entrepreneurial nature when you’re in these linear platforms because they are big organizations that move at a pace that’s very different.
Lilly Singh: Correct. It is not only the pace, but it’s also just the rules. It’s, I mean, a lot of these corporations are stuck in this, you know, old-school system that worked once upon a time, and they’re so against shifting any of those rigid rules. And I’m like, You will die. You are going — you are slowly dying. You are slowly bleeding out because you have no ability to be flexible and adjust to the times. And I am trying to educate you and adjust you to the times. So I think it’s just about, like — just because something I often get told is “But that’s the way it’s always been done,” that doesn’t make it right. That does not make it right. You need to be open to change. And I think I, as a person, represent that change. And so I think it’s really ridiculous for corporations to not listen to people like me.
Swisher: The Met Gala was a few weeks ago, for example, and people noted the lack of internet stars. You went in 2019.
Singh: I did.
Swisher: But Anna Wintour reportedly culled YouTubers and TikTokers from the guest list after getting complaints for having too many internet stars. What’s your reaction, and is there a difference between internet stars, except that you’re probably bigger than others these days?
Singh: Yeah. Thank you for saying that.
Swisher: It’s true. I’ve seen the numbers, so —
Singh: I will respectfully have to call it the hypocrisy of saying “I will not have internet stars there, but I will use one to garner views as she interviews people on the red carpet.” I think that’s an important part of that, because if there were truly no internet stars, then Emma Chamberlain wouldn’t be there. And previously that was Liza Koshy. You know, so I think there is a little bit of hypocrisy that happens where it’s like, “We will use you for your views and abuse you for your engagement when it’s convenient for us, but we’re not actually gonna value you as real talent.”
That’s something I’ve really had to deal with for a lot of my career, and again, I’m gonna go back to — just because I made content for YouTube and you made content for TV and film, it doesn’t make you better than me. Especially because, again, a lot of those people probably have way more views and are probably more well known than a lot of those stars. So I don’t even think it’s a competition. I think this whole idea of “What is a star?” — that definition has changed … There’s no difference to the younger generation at all. And I think the older generation’s just holding on to this idea of gatekeepers, and I’m letting you know it’s going to collapse. Very, very soon.
Singh: Can I add one more thing? ’Cause now I’m a little heated. Another thing I will say specifically about the Met Gala — and I’m not taking a crap on the Met Gala. I need to emphasize I think it’s a really cool event and really culturally significant. But if it’s about fashion, which it is, who has revolutionized fashion? It is the younger generations.
Swisher: And Jared Leto. But go ahead.
Singh: Correct. But I’m saying fashion is about breaking the rules. It’s about being revolutionary. It’s about showing up as your authentic self, and no one does that better than some of the people that were X-ed off that list, I would say. So it’s kind of like you’re also halting the revolution of fashion a little bit.
Swisher: Yeah, because Anna Wintour’s such a young and vibrant person. I said it.
Singh: You said it, not me. It’s okay. I’m still trying to get invited to the Met Gala.
Swisher: I don’t wanna get invited. I already interviewed her, and that didn’t go so well for her. Okay, anyway — so you’re also part of an earlier generation of YouTubers that are trying to make the shift to linear ’cause you do wanna get in that space. Why is that a goal at all?
Singh: You know, I have spoken about this in therapy so many times. Because the reality is there have been moments when I am sitting in my house and I’m like, Okay, you have accomplished so many vision boards. I’ve met every person I’ve wanted to meet. I’ve made all the money I’ve wanted to make. I have — there’s nothing. Why do I have this obsession with doing more, especially being validated by the traditional space?
And I think it has to do with a lot — the fact that I still grew up with TV and movies. You know, I’m not — I’m a millennial that grew up with those traditional stars. I think that’s gonna change with Gen Z. I think Gen Z now, they didn’t necessarily grow up with that. I think that’s why they consider me the same as a lot of these traditional stars. But I still have that itch in me where I’m like, No, I know what it feels like to love a movie star that was only — you could only see them in the movie. You couldn’t interact with them in any other way. And so I still have that desire.
And if I’m being truthful as well, it’s also because I’m so annoying and I wanna just prove so many people wrong. I wanna prove people right, but I also wanna prove people wrong. And I know that’s unhealthy and I should focus more on proving people right. But that’s me being honest, right? I want to prove people wrong.
Swisher: But you’re going from a younger audience, which is the up-and-coming, to an older demographic.
Singh: Correct. Because those are the people that need to be proven wrong!
Swisher: I did ask this to Jon Stewart of The Daily Show … I asked him how you maintain relevancy in this fast-media age. There is a pace that has changed rather significantly. What do you think is the best way to do that?
Singh: So I’m a big believer — I’m a businesswoman, clearly; look at my suit. But I’m also a very spiritual person. So I always try to combine business and spirituality. And my answer to that is I would argue that every single person is relevant and irrelevant at the same time. Because of how we consume information. Like, social media is an echo chamber. This is a prime example: How many of you have been obsessed with someone or watched a show and you’re like, This is the best thing. You go to someone, they’re like, “I’ve never heard of that in my life.”
Swisher: Yeah. A lot.
Singh: All the time. It’s because relevancy is so subjective. You know, people will come up to me and — user 6479 will comment on my post and be like, “Oh my God, you’re so irrelevant.” And I’m like, “I’m literally on a red carpet ’cause I have three shows. Like, who are you? Why are you —” It is just so subjective. And I think because of social media, we’ve lost this idea of things even being subjective. We think everything is a fact. We think opinions are facts. They’re not the same thing.
Swisher: Except that it does move faster. It does move faster. And it’s very hard for people to maintain one thing we all share together or something that everybody knows. So it’s split over and over again, which makes it more difficult to be impactful.
Singh: So maybe it’s something we should stop chasing.
Swisher: Fair point. Yeah. One of the things — we were just talking about diversity. I did interview Geena Davis. She pointed out that, often, male executives think there’s only space for one woman in a movie or film. After Thelma & Louise, she was excited about other films that executives kind of told her, “Oh, we’ve already done that.” What do you think has happened?This is something — this is 20 years ago she was talking about.
Singh: Yeah. It’s frigging stupid. It’s so stupid. This idea that they’re — honestly, what it is is a fragile system that’s scared. I think people are scared of women, and they should be scared of women. ’Cause we’re awesome. And we’re gonna crush things once we get there. A woman has to work, like, a million times harder to accomplish things. So imagine if you gave multiple women a shot. You know what I’m saying?
So for a lot of my career, I kind of subscribed to this idea. I was like, Oh my God, I can’t support another brown woman because, like, then I won’t get the brand deal. Then I won’t get the spotlight. And I have had to actively unsubscribe from that idea — because that’s what they want. They want me to sit there and be like, Oh, there’s only space for me. But the second we all are like, No, forget that. I’m actually gonna bring every woman to this table — that’s when change is gonna happen.
Swisher: Right. Do you feel in competition with, like, a Mindy Kaling or whatever?
Singh: One of the hardest parts of being a minority, looking like how I look — I won’t even say minority. Let me speak from my own experience: One of the hardest parts about being South Asian is that you see yourself so little onscreen. So you feel this need to be represented by the one or two things that are onscreen. And no human being can accomplish that. Mindy Kaling cannot represent 2 billion people. She can write from her experience, and she can create art from her experience. And so that is a challenge of being a minority creator, is that you have the pressure. Like, I kid you not — someone came up to me when my late-night show was announced and literally said to me, “Two billion people are counting on you.”
There is no way I will make two billion people feel seen and heard and talk about their experience because we’re all different. But when you have so little shows — so Mindy’s been crushing it for us, but people will give her flak and be like, “You didn’t do this, and you didn’t do that.” She is not the problem! The system is the problem! Because if there were a hundred shows featuring people that look like us, you would not be giving her that flak. And so really, give the criticism where it is due. It is not due at the minorities that are trying their best to make this happen.
Swisher: Absolutely. It was the same thing with gay people for many years.
Singh: A hundred percent.
Swisher: With that, you came out as bisexual in 2019. You said it was one of the scariest experiences of your life. Does that add on to it?
Singh: A hundred percent … It was so scary. It was so much pressure. I mean, it was the most unhealthy time in my life. But I remember after one of my tapings, I literally went back to my greenroom, and I made a list being like, How many times did I mention being a woman? How many times did I mention being South Asian? Did I do that enough? Did I mention being queer enough? Did I do it too much? Did I do it too little? Like, who wants to live like that? That’s not a fair position for everyone to be in. And we shouldn’t expect that of people.
Swisher: At the same time, there isn’t enough representation.
Singh: There isn’t. But there’s people mad on both sides because I didn’t say it enough and because I said it too much, you know?
Swisher: So what’s the solution in that way?
Singh: The solution is to say, “Eff both of you. I’m doing what’s right to me.”
Swisher: Okay. Just doing my story.
Singh: Yes. And I’ve learned, and I don’t even mean to be rude — it’s just the truth: I cannot please both parties. I can just do what I can do.
And going back to Mindy ’cause it’s how we all came from it: Every single time I’ve ever needed guidance or help or mentorship, she has immediately picked up the phone, texted me back, and helped me.
This interview has been edited for length and clarity.
On With Kara Swisher is produced by Nayeema Raza, Blakeney Schick, Cristian Castro Rossel, and Megan Burney, with mixing by Fernando Arruda, engineering by Christopher Shurtleff, and theme music by Trackademics. New episodes will drop every Monday and Thursday. Follow the show on Apple Podcasts, Spotify, or wherever you get your podcasts.
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