If you’re not already familiar with the work of actor and comedian Lilly Singh, you will be soon. After rising to stardom as a YouTube personality, aptly named “Superwoman,” 32-year-old Singh has gone on to make history as the first openly bisexual late night television host of Indian descent on an American broadcast network, with her hit NBC show A Little Late with Lilly Singh.

Working with Skillshare on her new original class, Digital Storytelling with Lilly Singh: Make Content People Care About, Singh dives into her storytelling process and shares her tips and tricks to help you create standout online content that fits with your creative goals, whatever your story is. But first, let’s get to know the woman behind the screen!

Early Life and Career

So who is Lilly Singh? Born and raised in Toronto, Singh had dreams of being an entertainer as long as she can remember, but never expected them to materialize. A self-styled “scrappy tomboy,” Singh is the embodiment of a first-generation success story. Her parents, Sukhwinder and Malwinder, immigrated to Canada from the Punjabi region of India in the 1970s, with her older sister Tina born in 1982 and Lilly following six years later. 

Lilly Singh as a child
Source: Instagram
Lilly Singh as a child. Lilly Singh’s parents Sukhwinder and Malwinder were initially hesitant of Lilly’s chosen career but have become her biggest supporters.

Her love for Dwayne “The Rock” Johnson, hip hop, and Bollywood were early signs of the characters she would go on to create under her Superwoman moniker. “Every other kid in school wanted to be a doctor, an engineer, a scientist, and my parents were like, ‘Oh, of course, our daughter wants to be a rapper,’” sister Tina, also a YouTuber, told Toronto Life in a 2017 interview. 

Singh quickly became hooked on bhangra, a Punjabi dance that’s commonly found in the closing scenes of every Bollywood musical and features elaborate costumes. Becoming president of the bhangra club in 2006 at York University, where she was studying psychology, was her first taste of the spotlight, and soon Singh was performing at weddings around Toronto. “My parents said, ‘No, girls can’t dance at people’s weddings, it doesn’t look good.’ Ultimately, they let me do it because I was going to do it anyway,” she recalls

After graduating in 2010, Singh divided her time between a job in a collections agency and volunteering at the Gursikh Sabha, a Sikh temple in Scarborough, Toronto (she no longer practices any specific religion, but openly believes in God). With no firm ideas on what to do next and struggling with depression, it was then that she discovered the platform that would change her life: YouTube.

Lilly Singh: YouTuber, Late Night Host, Author, and More

Early Days on YouTube

Plenty of YouTubers can attribute their lightbulb moment to the original pack of content creators like Shay Carl and Jenna Marbles. Lilly Singh is no exception. She jumped into creating her own channel after being inspired by Jenna’s personality-driven videos and Superwoman, a name taken from early 2000’s rapper Lil’ Mo, was born. 

After several months of releasing content, her video “Official Guide to Brown Girls” garnered over 10,000 views within a day. Plans for graduate school were indefinitely put on hold, and Singh’s new career as a professional YouTuber was underway. By 2013, she’d reached over one million subscribers and the next million quickly followed within a few months. 

Over the next year, the Superwoman channel continued to grow thanks to Singh’s quick-witted skits with outrageously eccentric characters, often parodying her parents and family members. “As a brown girl, I don’t think people expect me to say the things I say. And when I do, they’re like ‘Oh my god, I feel that way too!’” she told the Globe and Mail in an interview.

Collaborations with other YouTubers helped to take her channel even further and subscriber numbers rocketed into the millions, netting her a Shorty Award nomination for Best YouTube Comedian in 2014 (which she went on to win in 2015).

World Domination

By 2015, Singh began planning a world tour, which would be filmed as a documentary for YouTube Red titled A Trip to Unicorn Island. The show would be everything she had ever dreamed of doing as an entertainer, with bhangra-inspired costumes and dancers, rapping, and comedy sketches. 

Unicorn Island documentary cover
Source: Instagram
Lilly Singh’s YouTube documentary, A Trip to Unicorn Island, follows her 2015 sellout world tour.

It was also a chance for Singh to meet her growing nation of fans all over the world. With the documentary funding her plans, Singh toured across Europe, America, Asia, and Australia for most of the next year, selling out almost every date. Not only did the tour firmly cement Singh’s place in YouTube stardom, but it brought along a whole new level of influence and commercial notoriety. 

Brands like Coca-Cola were now knocking on her door, creating sponsored content on her channel, and flying her to the Rio Olympics. Skittles, Toyota, Smashbox Cosmetics, and more soon followed. The girl from Toronto, who once winced at the idea of spending $600 on a new camera, was now bringing in multiple five-figure brand deals, appearing on billboards in Times Square, and calling her childhood idols personal friends. 

Lily and the Rock
Source: Instagram
Lilly Singh with former childhood idol turned friend, Dwayne “The Rock” Johnson.

How to Be a Bawse

Having already proven her writing chops in her YouTube sketches and sold-out shows around the world, Singh turned her hand to non-fiction in 2017 with the release of How To Be A Bawse: A Guide to Conquering Life. The book went on to become a number one New York Times bestseller and won the 2017 Goodreads Choice Award for Best Non-Fiction. 

Lilly Singh's book
Source: Instagram
Lilly Singh’s How To Be A Bawse became a number one New York Times bestseller in 2017.

Her subsequent world tour, #BawseBook Tour was another huge success, with more sellout shows and partnerships with global brands like Calvin Klein and Pantene. Proving to the world that she had become the ultimate “bawse,” little did Singh know what was to come next.

The Lilly Singh Show: Making History On American TV

Never did she think that the words “Lilly Singh late show” would be thrown around a conference room, let alone in front of major American broadcast networks. But by 2019, that’s exactly what was happening. Looking for a replacement for Last Call with Carson Daly, a former producer of Late Night with Conan O’Brien suggested Singh thanks to her serious interview skills and comedic talent. 

Late Night with Lilly Singh
Source: Instagram
Making television history, A Little Late With Lilly Singh debuted on NBC in September 2019.

A Little Late With Lilly Singh debuted on September 16, 2019, propelling Singh into the mainstream media spotlight and firmly putting her name in the record books. After coming out as bisexual in February 2019, she is the first openly LGTBQ+ person to host a late night show on an American broadcast network, as well as the first person of Indian or South Asian heritage to do so.

The show features both in-studio interviews and pre-recorded sketches and monologues, with recording moving to an in-house setting for the second season due to the COVID-19 pandemic. Season 2 of the Lilly Singh late show premiered on January 11, 2021. Along with hosting, Singh is also a producer of the show under her production studio, Unicorn Island Productions.

What’s Next for Lilly Singh?

With a successful late night show, an ever-growing social media brand, and a New York Times bestselling book, the sky really is the limit.

And that’s the dream for Singh: to create a flexible and creative career that can bend as she wants. Telling Marie Claire in 2019, “My life has surpassed anything I could have imagined.” Her goal is always to make herself proud, “because that’s the only person I can control.” She’s certainly done that.

Where to Find More Lilly Singh

Keep up to date with all things Lilly Singh on her social media and website!

Share Your Story Online With Lilly Singh!

Digital Storytelling with Lilly Singh: Make Content People Care About