SuperWoman: The Lilly Singh Story

Is it a plane? Is it a bird? No, it’s SuperWoman! In 2011, Lilly Singh was in a deep depression. Society expected her to pursue a career she wasn’t interested in; start a family and live a “normal” life. Today, she’s filming S2 of her historic late-night talk show.

Here’s the abnormal story of the rise of Superwoman.

Early life

Lilly was born on 26 September 1988 in Scarborough, a suburban neighborhood in Toronto, Canada. Her mother and father, Malwinder Kuar and Sukhwinder Singh had moved to Canada in the ‘70’s. Her father tried working security and furniture sales before operating a chain of gas stations. Lilly and Tina, her elder sister, grew up as Sikhs.

Growing up, Lilly was an extrovert and a tomboy – she describes herself as the annoying kid at parties who would be the center of attention. Whenever someone asked her what she wanted to be when she grew up, she always said, “actress” or “rap star”. All throughout school, she thought she was destined for stardom. Lilly’s obsessions growing up included The BackStreet Boys and The Spice Girls. But her biggest hero was The Rock, aka Dwayne Johnson. In fact, her room was plastered with pictures of him.

Did someone say ‘Vision Board’?

The lead up to Lilly’s eureka moment

Her journey to stardom didn’t have the happiest of beginnings. After High School, Lilly didn’t know what to do with her life. None of the conventional career paths excited her but her Indian upbringing meant she had to make a choice between traditional careers. So she followed in her sister’s footsteps and signed up for a bachelor’s degree in psychology from York University.

During college, Lilly lost a bit of the mojo that made her, her. She knew in her heart of hearts that she wanted to be in entertainment. Instead, she was sitting in classes and doing assignments for her psych degree. This chasm between her reality and her dreams caused Lilly to fall into a depression in her last year at Uni. During this time, Lilly barely made it through school. She ignored calls from friends and just did the bare minimum to get through her coursework. She had nothing to look forward to and couldn’t find reasons to wake up in the morning.

It was a dark time. It didn’t seem like there was any answer. She just couldn’t imagine spending the rest of her life in a traditional 9-5. At the same time, she couldn’t think of anything better that she could do either and when her father recommended she do her Masters after she finished her current course, she spiraled even more.

It was during this time, that a depressed and confused Lilly stumbled upon a video on a streaming platform called YouTube. The video was by Jenna Marbles and it was filmed in her bedroom, on a laptop camera. But the video was seen by millions of fans.

A light bulb went off in her head.

Lilly was always a natural performer- she used to do sketches for her family; rap and act for her friends and classmates.. doing the same for video would be a natural process. So Lilly opened an account with YouTube in 2010.

Her start on YouTube

She branded herself as ‘Superwoman’ and decided to broadcast herself.  Why the title “Superwoman?” Well in her words, “Lilly sometimes gets scared, sad and tired whereas Superwoman is a performer – she will never get scared, sad or tired. She is super-confident all the time.”

Her first video, a poem on religion, only got 70 views, but Lilly was over the moon. This positive reinforcement following the bout of depression kept Lilly going. She began experimenting with different formats and styles, from rap music videos to sketches.

Slowly but surely she climbed her way out of the dark well of depression. She still had to go to classes but at least now she had something to look forward to before and after class. Being creative on the internet had reconnected her to the parts of herself that she had forgotten. Parts of herself that she loved.

It was at this time that she posted the video, ‘Official Guide to Brown Girls.’

The video was a comedy skit about the funny dating habits of Indian women and men. The night she posted it, her phone kept ringing all night with messages from random fans. It earned 10,000 views in 24 hours. It was the first time she understood how quickly one video could bring her attention. For some time, her parents had no clue about her newfound hobby but soon family members started calling asking them if they had seen her videos.

Once they saw the videos, they became fans, on one condition. The videos should not interfere with Lilly’s education. By the end of 2011 however, Lilly had been posting on YouTube sporadically for over a year. Her college had come to an end and she had to make a decision about what she was going to do with her future, aka what subject she was going to choose for her Masters’s.

But during a family holiday in the Dominican Republic, Lilly chose to make a choice. There as she was walking by the beach by herself, she asked herself what she wanted from life- when she actually felt happy and she realized the answer to that question was when she was entertaining people.

So she told her parents that she wasn’t going to continue her education but instead she was going to make YouTube videos. It was the only part of her life where she was actually doing what made her feel alive-she wanted to double down on it.

The life changing decision

Her parents were taken aback at first. To her traditional Indian parents, the whole concept of “this YouTube thing” was far-fetched. In fact, any career in entertainment sounded like a pipe dream to them. Something that shouldn’t even be considered; much less make it to a list of options. It just made more sense for her to pursue her Masters. After a bit of back and forth Lilly convinced her parents to let her pursue this YouTube thing. They agreed, under one condition-she could do it for one year. If at the end of one year, it wasn’t working out, she’d have to get back to the tried and tested path.

She threw herself into YouTube, posting multiple times a week knowing almost nothing about professional camera angles, lighting or video editing. She invested in a 600$ camera(a huge buy for her at the time) and went about creating videos obsessively. She made videos about her life as an Indian girl in the States- highlighting the expectations that came with the same.

In 2012, she made the video, “Sh*t Punjabi Mothers Say”. This video was the first time we were introduced to the alter ego of Lilly’s mom, Manjeet. Soon, she made a satirical character based on her dad as well, called Paramjeet. The characters would become a mainstay in her videos. Throughout 2012, she hustled. She posted several commentary videos, where Lilly talked about different things that were happening in and around her life. From things like her dating life to more serious issues like gun rights, Lilly put her thoughts out there. All with her signature Superwoman quirk, of course.

This initial period was in no way easy though. She was living with her parents and had to make her own moolah. Initially, the paychecks from YT were tiny-her first invoice from YouTube was about $18. So Singh made ends meet by emceeing events around Toronto.

The rise to fame

With her videos she was quickly adding new subscribers.

Her audience included mostly 14-25-year-old women. But she was adding more parents and guys as well. The numbers though would always be second priority for Lilly. What mattered most to her was that she was making a positive impact on whoever watched her content. By the start of 2013, her hustle had paid off. She had amassed a subscriber base of close to 200,000 subscribers-blasting past the goals that she had set for herself.

Her parents were surprised but supportive. As long as she was working hard and seeing results, they were coming along for the ride.  Over the course of 2013, she added close to a million subs.

She even began the next trademark of her career-awesome collaborations. In 2014, Lilly collaborated with several of YouTube’s biggest creators of the time including Fouseytube; Conor Franta; Ryan Higa; Rhett & Link; Shane Dawson; Tyler Oakley; Timothy DeLa Ghetto.

She also made collabs with movie stars-something quite rare for a YouTuber at the time. She got Madhuri Dixit, the Bollywood superstar to collaborate with her on a video. Plus, big names like Kunal Nayyar, Seth Rogen and James Franco all made collaborations with her.

It would be beginning of her entry into mainstream culture.

Going Mainstream

She hit the 2 million subscribers mere months later. With her rapid growth, by the end of 2014, Lilly started getting the attention of smart marketers. The kind of attention that any creator would kill for. Skittles, TD, Toyota and Smashbox were some of the brands that signed up for some Lilly magic. They commissioned her to make content for them. And soon, the biggest brand in the world came knocking, Coca Cola. Coca Cola made a substantial investment in Lilly. For example the brand flew her to the Olympic Games in Rio to create live- streaming content for Coca-Cola and they even agreed to finance parts of what would be her biggest project yet.

A Trip to Unicorn Island.

A trip to Unicorn Island was Lilly’s first real step outside of the YouTube ecosystem and in classic Superwoman fashion, that step was a leap.

AT2UI was an ambitious 27 city world tour where Lilly sang, danced and acted out some of her most famous YouTube bits. The whole trip was documented and made into a feature film that premiered on YouTube Red. India, Australia, Hong Kong- these were just some of the places that Lilly hit up on her tour. The film based on the tour even won the Streamy for best feature film that year.

But the highlight of 2015 for Lilly?

She would say…it was meeting The Rock.

The pair met at they year’s MTV Movie Awards. Remember the vision board with pictures of him? Safe to say she willed her dreams into existence with sheer hustle.

By the end of 2015, Lilly Singh, the brand was getting much too big for the city of Toronto. To really take her career to the next level she had to go to the entertainment capital of the world-LA.

So at 26, Singh finally moved out of her parents’ house and to L.A. She rented her first apartment in Mid-City (she dubbed it the “Lillypad”) and got down to business.

The L.A. Chapter

With her over 7 million subscriber count and huge brand associations, Lilly was a legitimate celebrity. She had proved capable of both filling up seats and getting eyeballs on a video. With those credentials, she made her first appearance on Fallon. From there she would go on from strength to strength. In 2016, Variety magazine recognized her as one of their 10 Comics to Watch. She won two Teen Choice awards. She was even ranked on Forbes 30 under 30. Lilly also got the Rock and Priyanka Chopra to collab with her.

For the next couple of years, this upward climb stayed strong. Lilly released her first book, an autobiography called How to Be a Bawse-it topped the NYT best seller list. She also acted in Fahrenheit 461 with Michael B. Jordan and collabed with people like Charlize Theron, Bill Gates and Will Smith. She also opened her own production studio, Unicorn Island.

By November of 2018, Lilly had been making content for YouTube for 8 years straight. She was producing as many as nine videos a week, dozens of tweets and Instagram posts. This is not even counting the work she was doing outside her channel.

And the output took its toll.

Superwoman announced that she was taking a break from YouTube to focus on her mental health towards the end of 2018. For a few weeks, she took time away from the platform to get a therapist; call her friends and rethink her content.

She came back a few weeks later, refreshed and in, Feb 2019, Lilly Singh came out as bi-sexual. The decision was a hard one considering her traditional Indian upbringing and the fact she could lose a part of her fan base because of it.

But she did it anyway, as she felt she needed to embrace her “obstacles as her superpowers.”

Making history as the first queer brown talk-show host

Lilly got her own NBC late night talk show- A Little Late with Lilly Singh.

The show is a historic first for many things(eg:- First time for a queer woman to host a Late Night Show). Today, Lilly Singh is filming the second season of the show. She’s also busy filming episodes of her second show with NBC, called Sketchy Times with Lilly. She has 14 million subscribers and a net worth of an estimated 20M$.

A mere 9 years ago she was a girl in a bedroom with a camera.

Her key to success

She thinks a large part of it is the hustle she’s picked up from her father. “If you lie down at night and you don’t feel utterly exhausted,” Lilly explains, “then you, my friend, do not want it bad enough.” We think the other ingredients of her success is her authenticity; her versatility and her infectious positivity. All super qualities. So super, that before she got on her talk show, she let go of the Superwoman moniker. And began to refer to herself as simply, Lilly.

In Lilly’s words, “as people we have all the tools we need to be our saving grace. Today as I type this, as the person I’ve grown into, I feel even more empowered by the name Lilly. Lilly has become an even bigger hero than Superwoman on this journey through my life.”

We couldn’t agree more. So, it’s not a bird. It’s not a plan. It’s yo gurrrrllll, Lilly Singh.

What’s Lilly been upto lately?

After 2 seasons and 161 episodes, Lilly left her Late Night host duties to get back to her bread and butter- Skits. But unlike before where these skits played on YouTube, now they’ll be aired on primetime NBC on a show called “Sketchy Times with Lilly.” Lilly also announced that she’s working on a Netflix comedy project with Kenya Barris, the writer of ‘Black-ish’.

But why the move away from Late Night? In Lilly’s words, she has the desire to “make longer-form content telling underrepresented stories” and “to bring diversity to the screen in an even bigger way.”

More power to you, Lilly!

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