After years in Hollywood, Singh opens up about why she’s stepping back into character comedy on her own terms.
Oct 15, 2026 [[read-time]] minute read
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A New York Times bestseller. A late-night television show. A seat in executive pitch meetings. There was a stretch where creator success meant doing whatever it took to graduate from the internet. Lilly Singh achieved all of that. But today, she is returning to form.
In 2010, posting to YouTube as IISuperwomanII from her bedroom in Scarborough, Ontario, Singh was among the first wave to prove online sketch comedy could build a massive global following. Her hyper-relatable sense of humor and exaggerated characters quickly turned her into one of the earliest and most recognizable faces on the platform.
Now, after building a career in Hollywood, Singh is releasing her first major sketch in years titled “My First Day Back at YouTube." We caught up to talk about what brought her back.
You were, in many ways, the face of YouTube creators crossing into network television. Looking back, what drove that initial desire to enter traditional media?
Lilly: It's always been about storytelling. There are different platforms for different types of stories, and as a creator, I'm just curious to try all of them. What does it feel like to make TV? A feature film? A YouTube video?
Plus, I grew up purely on traditional media—there was no YouTube or Instagram back then. So, of course, I had that natural curiosity. Even today, I love TV and film. But there’s something uniquely magical about YouTube. It’s where my true community is, and no matter where I've worked, I've always felt that.
What worked well for you inside that space, and what creative freedoms did you miss from working independently?
Lilly: On projects like Dollface or The Muppets, what I fell in love with was the collaboration. On YouTube, it was usually just my point of view and my vision alone, which is great sometimes. But on set, I learned the value of having entire departments who elevate a story with props, set design and writing.
That said, I’ve now taken those learnings and implemented them into my YouTube work. For the decade that I made YouTube videos, it was for the most part a very scrappy, small team. I like the inherent DIYness of that, but this time I plan to have proper art and production departments where I can feel like I'm part of a creative team instead of carrying everything on my own shoulders.
What works better independently comes down to freedom. Hollywood has real systemic issues, especially for women and people of color. Over the past few years, I received countless notes that weren't about improving the project, but about making it "more palatable," "more marketable," or "less niche." That is fundamentally anti-creative. Our job is to tell our stories unapologetically. On YouTube, there are no gatekeepers demanding I make my brain baby more palatable for the masses. That authenticity is why my channel worked in the first place.
It feels like the power dynamic inverted while you were there—creator-led indie projects are now driving culture in ways traditional networks struggle to do. What does watching that transformation feel like?
Lilly: Honestly? It’s almost as if Hollywood doesn't run on logic or evidence, but purely on old habits. Even with runaway hits like Barbie or Sinners, executives treat them as flukes. To me, it's always been a no-brainer. The data clearly shows audiences show up for diverse stories, yet in every general meeting, I’m still told my pitch is "too niche."
Meanwhile, this new wave of creators is refusing to water things down. In India right now, people are making hilarious content in all their regional dialects. If young Lilly had seen that, she never would have felt like a minority for a second. And creators like Druski are completely changing the game by saying: "If you want me, you come into my world. We’re not changing what works." I was caught in that earlier era where the industry said ‘we're going to take this person and put them into the system that is so not them and try to make it work.’ Seeing these new creators stand ten toes down inspires me to stand ten toes down too.
Why did now feel like the right time for a return to form?
Lilly: I'm going to keep it 100: this past year has been a tough health year for me. Not expressing myself through videos and making content literally made me feel sick. My nervous system and immune system felt so restricted working in a system that didn't let me express myself.
Coming back isn’t about proving Hollywood wrong — it’s as simple as joy. Dressing up as characters gives me purpose and makes me excited to wake up in the morning. When I first did this, I was building my career. I had bills to pay, had just moved to LA, and had to grind out uploads every Monday and Thursday alongside daily vlogs. Now, I’m in the very privileged position of having built stability. I get to play, make things that make me laugh, and have fun. Creating from pure play instead of intense pressure changes everything.
How has your comedic voice evolved over the past decade?
Lilly: The core stuff is part of my DNA—observational comedy, situational humor, dressing up as characters. That won't change.
What has evolved is my perspective. Back then, I made sketches about school and teenage crushes. Now, you’re seeing an adult Lilly who is self-assured, knows who she is, and isn't seeking external validation. I’m much more steadfast in my point of view. I don't punch down or try to be edgy—that’s never been me. My comedy is about making people feel seen. The best compliment I ever get is, "I thought I was the only one." That’s what I care about.
You have a massive global audience across Canada, the US, India, and beyond. How does that shape your approach?
Lilly: That was actually a huge factor in relaunching the channel! I did a feature film recently, Doin' It, which I love and am so proud of. But because of how traditional distribution deals work, so many of my longtime fans in India, the UK, or Trinidad and Tobago couldn't even watch it.
YouTube’s superpower is global distribution. When I write in Hollywood, I often have to halt the momentum for clunky exposition, like having to explain what Diwali is. It kills creativity! On YouTube, I don't have to over-explain a Punjabi or Caribbean concept. The audience is already there, and they're either in on it or excited to learn. When comedy gets specific and nuanced, it actually gets funnier. That freedom is what I missed the most.
What was it like collaborating with Alan Chikin Chow and Jeenie Weenie for your comeback sketch?
Lilly: Amazing! When I was developing the concept, I really wanted a few cameos. Alan has been such a vocal supporter of mine for years, he even sent me a magazine cover once where he was wearing my Superwoman ring, so having him play the liaison welcoming me back was just perfect. And Jeenie crushed it, too.
That first video had to do a lot of heavy lifting: announce the relaunch, set the tone, bring back fan-favorite characters, and give something sentimental to the OG Team Super fans. The upcoming content is for everyone, but that first one was strictly for the day ones.
Having achieved all the big milestones — the show, the subscribers, the views — what does success look like for you today?
Lilly: The mentally healthy version of me speaking today hopes (and I say hope because I'm not sitting on a high horse pretending I've got it all figured out) to stay completely disconnected from the metrics that used to drive me.
Success is no longer killing myself with uploads every Monday and Thursday, or burning out chasing a viral video. Success now is asking: Can I push myself creatively? Can I elevate the writing, the acting, the production? Can I take ambitious ideas I thought could only live in Hollywood and actually build them right here on YouTube?
Above all, it’s about experiencing genuine joy. Wrapping that first sketch a few days ago, the happiness I felt on set was something I hadn't felt in five years. That feeling alone is success. I even told my therapist: "You will remind me of this answer a year from now!" because creators are so much more than just views and analytics.