Can an online star really make it in Hollywood?

Lilly Singh, Issa Rae, and others have made the leap from online auteurs to bona fide TV personalities. Not everyone who hopes to turn followers and views into a mainstream career succeeds.

In one of the first desk segments of her new talk show A Little Late, host Lilly Singh joked about sending Harvey Weinstein a house plant. Because, she pointed out, “No other living thing wants to be near you right now.”

The joke fit well with the irreverent comedian’s point of view. When Singh’s A Little Late made its debut on NBC in September, she became the first bisexual woman of color to host a late-night talk show. Singh, who favors brightly colored pantsuits and sneakers, delivers high-energy monologues that avoid explicitly political material but don’t shy away from uncomfortable topics such as Weinstein. She also deftly engages celebrity guests such as Charlize Theron, Snoop Dogg, and Ewan McGregor in comedy bits.

For those looking at the ways in which web culture and “mainstream” media have blended together, there are few better examples than Singh. Singh got her start making videos for YouTube in 2010 while living with her parents in Toronto after graduating from college, eventually becoming one of the platform’s biggest performers, with 16 million subscribers.

On A Little Late, Singh doesn’t veer too far from the tone of her most popular YouTube videos; on her personal channel, she focuses on comedy shorts about experiences including going clubbing, having long hair, and her Indian heritage. Guests aren’t new, either. She’s long had occasional collaborations with other well-known YouTubers, as well as famous folk attracted to her online fame (Dwayne Johnson became an early ally because his daughter was a Lilly fan). Like many YouTubers, she is simultaneously auteur and protagonist, creating a distinct persona — not too different from what hosts such as Jimmy Fallon and Stephen Colbert have done every night for decades.

That Singh, with a little pluck, could rise from DIY YouTube roots to broadcast television in less than a decade isn’t all that surprising. As long as Hollywood has existed, its elusive glamour has been coupled with origin stories about how anyone can break in given the right combination of opportunity and talent. Lana Turner was discovered sitting at the counter of a soda fountain. Steven Spielberg tells stories about sneaking onto the Universal Studios lot as a teenager. The Wachowskis painted houses and wrote comic book scripts before creating blockbusters.

But in the 2000s, when online platforms such as YouTube, Twitter, Vine, and Vimeo began giving aspiring filmmakers, comedians, and actors the opportunity to share their voices with the digital world, a new kind of success story began to emerge, thanks to the low barrier to entry. All you needed was a camera and something to say.

Issa Rae’s YouTube series The Misadventures of Awkward Black Girl eventually led to Rae creating and starring in the HBO comedy Insecure. Dan Harmon, the writer behind NBC’s Community and Adult Swim’s Rick and Morty, first developed his voice and cultivated industry relationships with the website Channel 101. Ilana Glazer and Abbi Jacobson made their cult-favorite comedy Broad City for YouTube before signing a deal with Comedy Central. The tender-hearted pot anthology series High Maintenance transformed from short-form installments independently posted to Vimeo by creators Ben Sinclair and Katja Blichfeld to a half-hour HBO comedy that sacrificed none of the original series’ charm.

Since those early days, digital platforms have beckoned people who want to gain a larger audience not just online but in mainstream “legacy” media. The examples above, and many more, quickly created the notion that anyone could use the web to get discovered and break into an industry that might previously have seemed insular. Unfortunately, it’s as exaggerated as the story about Spielberg breaking into Universal sound stages (he was actually an intern in the editorial department as a teenager). Making content for the web has helped some prove their abilities as showrunners and performers; for others, it has led to disappointment.

Using YouTube as a stepping stone

The reasons independent creators came to YouTube and other platforms during the latter years of the 2000s with original stories are varied, but there are some common themes: They had specific points of view for which they wanted an outlet, they hadn’t found opportunities within the established Hollywood system, or they craved the independence that creating their own content would offer them.

But back then, the idea of making a living off of those videos you made for the web didn’t necessarily seem like a possibility. For many, the idea was instead to start online, show what you could do, and then use that material as a stepping stone to bigger things: a big-name agent, a development deal, another show with a bigger budget. It was a path similar to how some filmmakers look at the independent film circuit as a first step to more mainstream work. But instead of trying to make a sale at Sundance, the entire internet was potentially a marketplace.

In the case of Singh, whose show returns with new episodes in 2020, her ascension from YouTube to broadcast TV came when executive producer John Irwin, who has worked frequently with NBC, was tipped off that the network was looking for somebody to fill the late-night slot. Singh made sense to him as a host; he’d previously scouted her videos as part of his company’s ongoing development process and noticed something about the variety of content Singh would make for her channel.

“Most of the time when people step into that job, they don’t know how to do the interview part,” Irwin said. But as part of her regular YouTube output, Singh had not just created comedy sketches but also interviewed Charlize Theron, Will Smith, Bill Gates, and Michelle Obama.

YouTube has become a vehicle for so many stars to showcase their abilities. It was how Hannah Hart, an independent creator, kick-started her career in 2011 when she got drunk one night and decided to film herself making a grilled cheese sandwich. The first My Drunk Kitchen video has been watched by 4.3 million people and was just the beginning of Hart’s career as an actor, author, producer, podcaster, and TV host.

Rich Fury/Getty Images for Teen Vogue

Michael Buckley wasn’t drunk when he started his YouTube channel. Instead, in the summer of 2006, the aspiring host started making videos as a way to show off his on-camera skills. His videos featured him ranting directly to the camera, The Daily Show-style, on topics like Beyonce’s feuds, Lindsay Lohan’s antics, and reality TV with unapologetic bluntness and wit.

“The thought of developing a following — I didn’t even know what that was at the time. My hope was just to practice being on camera,” he said. Then he made a video that got 200,000 views. “That’s when my brain was like, ‘Oh, wow, there is something here.’”

Buckley quickly became one of YouTube’s most popular personalities, success that translated into being featured in the New York Times, an HBO development deal, and, thanks to winning an online contest, a guest appearance on the talk show Live! With Kelly in 2012. His brand sponsorship deals, plus YouTube advertisements, enabled him to make six figures for years, he says — all from his Connecticut home.

Having friends in high places

Stories of YouTubers who go mainstream have helped feed the narrative that success is possible if you hustle and put yourself out there. But there’s a crucial component to that equation: making sure the right person sees your work.

This is not unique to web creators. At the beginning of his career, Conan O’Brien’s time on camera was limited to cameos on Saturday Night Live while he was a writer there. When SNL creator and Late Night executive producer Lorne Michaels went looking for the successor to David Letterman in 1993, O’Brien was writing and producing for The Simpsons. Michaels took a chance on the writer, and his faith led to the creation of a new late-night television star. Without Lorne, Conan may have never left the writers’ room.

Norman Ng/NBC/NBCU Photo Bank

While Singh’s huge online audience was a selling point, Irwin said that, for him, numbers weren’t a part of his scouting process. “I didn’t just look to YouTube to find somebody. I basically was looking everywhere. It’s all about the person and their talent,” he said.

In 2010, when the creators of Broad City started posting their YouTube series about two best friends getting high and trying to thrive in New York City, they did not get tons of views. But Glazer and Jacobson were students at the Upright Citizens Brigade comedy school, which was co-founded by Amy Poehler. Poehler, an established comedy figure after seven years as a Saturday Night Live cast member as well the new star of NBC’s Parks and Recreation, recognized their talent, and, as an executive producer, helped get the young women into the right rooms.

High Maintenance began life as an independent series, but creators Sinclair and Blichfeld also had no shortage of industry contacts, because Blichfeld was an Emmy-winning casting director for 30 Rock. After The Misadventures of Awkward Black Girl went viral, Rae partnered with renowned writer, producer, and performer Larry Wilmore to get Insecure off the ground.

“There are many creators whose shows were not popular online, but they were well done,” said Aymar Jean Christian, associate professor of communication at Northwestern University, who for years has studied the rising tide of independent digital creation. “And they’re now working in legacy media because what they did was good, and when they showed it to an agent or just an executive, that person was like, ‘You have talent so I’m going to put you in the industry.’ ”

Irwin said that he respected the fact that digital platforms do provide creators an opportunity to hone their abilities, but that they aren’t the only answer when it comes to discovery. “If CBS came to me and said, ‘Hey, we want our own Lilly Singh, let’s go to YouTube,’ I’d say, ‘Well, that’s not really the way to do it.’ You gotta go try and find the right person, wherever they are.”

Even getting seen by the right person isn’t a guarantee for success. Buckley’s 2008 HBO development deal meant a monthly paycheck from the network, which doesn’t necessarily mean a show will actually come out of it. And like many of the hundreds of development deals that get signed in Hollywood, Buckley’s never resulted in a show. He was making additional money from his sponsored videos, but three or four years into his YouTube career, he was exhausted by the grind.

“I was tired of being a one-man YouTube band, and anytime I would go and do TV, I’d be like, ‘Oh, this is so easy. Compared to what I’m doing, this is simple,’” he said. “But by that point my YouTube popularity had waned, and I was also graduating out of the celebrity pop culture type of commentary that people wanted me to do. I was going on these meetings and trying to sell myself as a pop culture commentator when I was losing interest in the topics and the celebrities and even the style of comedy that I had become successful for.”

Buckley’s experiences with wanting to break into the Hollywood establishment but not succeeding are not uncommon. “Every digital creator I’ve ever communicated with is interested in a bigger platform,” Christian said. For his 2018 book Open TV: Innovation Beyond Hollywood and the Rise of Web Television, Christian interviewed more than 100 people working in the digital space, including Rae and Glazer. “I don’t think I interviewed one person who said they rejected Hollywood completely and would never participate.”

The problem is the gatekeepers. “The leading networks and production companies, from casting to writing, will look at someone who’s done digital work, but they don’t view digital work as equally credible to mainstream work,” Christian said.

As the founder of OTV, a Chicago-based platform for intersectional television, Christian also helps artists from a wide range of backgrounds and points of view create their own shows. But a big factor in his advice to them is, “If your goal is to make it into legacy media, I recommend people just make content that’s recognizable to legacy media.”

Which, as Irwin observed, is exactly what Singh and others like her had done.

“New media is still new, and Hollywood is still run by people who did not grow up with the internet,” Christian said. “Years from now, we might be having a very different conversation.”

Johannes Eisele/AFP via Getty Images

Moving on from online stardom

After her early viral successes, Hart kept making My Drunk Kitchen because, in her words, “I enjoyed it.” But her hope back then was also, “Maybe if I make enough online content … someone will want to publish a book by me.”

Hart’s journey to that goal made her one of the first YouTubers to publish a book (she would soon be followed by many others), but it took some time. Meanwhile, in Hart’s first year on the platform, she made, in her words, “$18,000 — with YouTube being a very small portion of that.”

Thus, the lesson for her has been diversifying her various projects, from the Tasty/Facebook original series Edible History, to podcasting, to her newest book, titled My Drunk Kitchen Holidays! How to Savor and Celebrate the Year: A Cookbook.

Buckley is also exploring new interests. While he’s still occasionally making videos, he’s refocused his energies into a business as a life coach. “I’m really grateful for the opportunity, for the money, and for the brief moment of celebrity,” he said of his past on YouTube. “And I’m so thrilled to be in a very different chapter of my life.”

J. Countess/Getty Images

And what does Hart tell those who might ask her for advice on making it big on YouTube? “For me, I really always say, you have to focus on your voice and your message and why you want to do it. If you’re doing it to be famous, you’re always going to be chasing something that you’re never going to have.”

Liz Shannon Miller is a Los Angeles-based writer and editor who has been covering pop culture for more than 10 years for publications including Vulture, Variety, the AV Club, and the Hollywood Reporter.