Ellen, Analog, Amazing Race: YouTube Star Tyler Oakley Wants to Do Everything But Fail

Photo: Laurel Golio/Laurel Golio

When Tyler Oakley first started his YouTube channel in 2007, he was a freshman at Michigan State University with a webcam. Gay, fiercely opinionated, and known to drop an F-bomb or ten, he gradually attracted an online fandom before the term for his kind of following had a name. “Well helloooo, everybody, my name is Tyler Oakley!” is now the high-pitched greeting heard 'round the world daily by some 8 million subscribed to one of YouTube's most successful channels. In the nine years since his channel went live, Oakley's “people” (as he affectionately calls them) have watched his internet personality grow from rant-style vlogs, to sardonic pop-culture commentary, to shameless fangirling, to gay-rights advocacy and fundraising for the Trevor Project, to a more recent shift in offline branding. There's even a video dedicated to his YouTube history. But Oakley, a 27-year-old, formerly pastel-haired Michigan native, boasts ambition that might even outstrip the platform that launched him to internet stardom.

As YouTube becomes more and more mainstream, Oakley has stretched his reach to include Binge, his debut New York Times best-selling book; an international tour called Tyler Oakley's Slumber Party; and Snervous, a feature film that documents his life on tour. (It's a portmanteau his mom coined for feeling scared and nervous, in case you're wondering.) Not to mention a month spent globetrotting for The Amazing Race’s first-ever internet-celebrity season — on which he and his best friend finished third — and signing with Ellen DeGeneres's newly launched Ellen Digital Network. Yesterday, his new talk show The Tyler Oakley Show debuted on that platform.

Typically candid and admittedly still processing his celebrity as it grows by the day, Oakley shared his thoughts with Vulture on the fluidity of internet fame, the importance of safe spaces online, why traditional TV should already fear YouTube, and #TeamInternet’s breakout year.

You've starred on The Amazing Race and now you're Ellen DeGeneres's protégé. Do you now see yourself as more of a brand than a YouTube star? You're already the Ellen or Andy Cohen of the internet.
If you start buying the hype, you turn crazy. I've seen people just drink their own Kool-Aid. Cool things happen and that's because of the people who watch, and I'm lucky enough to have joined YouTube early and maybe done a few right things to elevate my channel to a place where it is now. And I don't for a second take it for granted. But do I think of myself as more than a YouTuber? I don't know. [Shrugs.] I don't really know. Nowadays, there are so many mediums that me and my friends can try to do. People don't really know what the next step is gonna be or is supposed to be for a YouTube person. So when I think about my friends who are killing it with movies or books or TV shows or podcasts or whatever, it's like, "Yes! Kill it." Keep doing it, because it's breaking down these boundaries of "Oh, they're just a YouTuber, they can't …" whatever. And I'm seeing all of my friends be like, "Ha, we will." And then they do it.

From the start, I've always said if I'm going to do something bigger, I want to do it with Ellen — on my vision boards and in my videos over the past eight years, I literally say that! — so it was a no-brainer for me. There are so many things about Ellen and Andy that I admire, but, with a cheeky grin and a wink, I'd rather say I'm the Tyler Oakley of the internet.

Up until last year, your eighth as a creator, I think people saw Tyler Oakley as just a YouTuber. What was your strategy for finally branching out?
I started to see other people doing other projects and thought, Okay, if I wanted to, what would I try if I knew it wouldn't fail? After seven or eight years of making videos, it can kind of become formulaic, especially if you're doing it every week at the same exact time. Having a podcast, for one, just felt so refreshing. Since it's unedited and conversational, it felt like a new way to approach pop culture. Going on tour let me finally interact with a roomful of people and have it be in-the-moment, sporadic, and completely unique at each stop. The YouTuber summer camp, co-hosted with Bethany Mota, was my favorite experience with viewers I've ever had. So many of them I already knew. It was great to finally meet them, but it was even better giving them a safe space to meet each other. The book was an opportunity to dive deep into subjects that I felt were maybe a little more serious, or harder to condense into a five-minute video.

Binge includes stories about domestic violence and an eating disorder that you kept from fans, which is surprising given how much of your life exists online. Why wait to tell them for almost a decade after you started your channel?
For personal reasons — it was therapeutic for me to work through things as I was writing. A lot of the subjects I wrote about that were more difficult, I thought, Okay, I'm just gonna write it and if I don't feel comfortable, it can just be a journal entry and doesn't have to make it into the book. Then when I wrote it, I felt ready to share those things. If people can read those stories and feel less alone, that felt important for me to put in the book. Untold stories were always the thought behind the book. I want it to be worth people's money. I didn't wanna put out something that is just merch in book form.

Will there be a sequel?
It's so funny because everyone's like, "That must be it. What else could you possibly have?" And I'm like, "Those were the tame things." That was to make sure I'm allowed to write a book. Now that the book did good — did good? Ugh, I'm a writer [laughs] — did well, I can bust out those juicy stories.

Do you need a clear line between your life and what you tell your audience? YouTube is this unprecedented industry where your life is literally your job. There's reality TV, of course, but you and so many others upload your lives to the internet.
I'm pretty conscious of that line, but I try my best to steer clear of it so it's not so obvious that I have that line. Because I share what I share so freely, I think people don't even think about what I don't share. They don't notice that there's stuff not in the story.

Are there still things you won't share?
Plenty. Some of my favorite YouTubers, it felt like I knew everything about them. But now that I might be friends with them, I realize they're only sharing 25 percent. There's plenty in my other 75 percent, like a lot of personal relationships, friendships, family stuff. I started to creep into sharing those things with the book and doc, but it's on my terms.

It reminds me of the scene in Snervous where you meet with your dad. We don't often get to see how coming out is an ongoing process for everyone involved. It's such a touching, unguarded moment for you both.
It was hard! It was really important to show that in the doc because we'd had ups and downs for over a decade. I wanted to include it because it felt like it was bigger than just me and my dad. If there are kids watching it and they're like, "My dad hates me or doesn't get who I am," I don't want them to think that's the end of the sentence. I wanted them to see that maybe your dad can come around. Maybe it will take years, but it's possible. Coming out is not, "You came out, you're done." My favorite thing now is not just coming-out videos, but "Coming Out: One Year Later" or "Coming Out: Ten Years Down the Line" and seeing the progression and what really happened after that moment.

What makes YouTube so particularly attractive to queer people, as well as communities of mental illness?
Traditional media hasn't really been a great place for disenfranchised voices to tell their own stories. I think about when I was growing up, about the few gay characters I could look at as role models. Lesbian characters, even less. Bi characters, even less. Trans characters, even less. And then all of those as people of color? Way less. Even with how much that has changed from then to now, often those characters are still being written by people that aren't actually representative of those groups.

But now marginalized people can speak for themselves on these platforms, and the audience is choosing the people instead of the people being presented to the audience. It's one of the first times it's gone the other way. It's also intimate. You're watching it alone with your headphones on and you're this far away from your computer, and they're this far away from their camera. A TV just feels distant.

You have an upcoming cameo on The Real O'Neals. What did you think about Noah Galvin's criticism of the way Colton Haynes came out?
Well, I'm friends with both of them, so what I think of this specific situation has already been discussed with them! But as far as coming out goes, there is no right way to come out and there is no right time to come out. It's always completely personal.

Snervous considers your role as a celebrity, which is still a fairly taboo concept in the YouTube world. YouTubers even dislike calling their subscribers "fans." Why document this unspoken part of the industry?
There's a couple reasons why this film exists: One, very selfishly, I want a scrapbook from back in the day when I did a tour just to have that for myself. Two, something for superfans, whether they came to the tour or not. Especially since I've been doing what I do for eight years, they've gotten pretty used to how I present myself. But to give them a completely different perspective, or more through another lens, felt like a good opportunity.

And then for people who have no clue who I am — which is a lot of people — and people who don't necessarily get what YouTube, fandom culture, or internet phenomenons are, I think it's a good introduction. Hopefully, the doc gives a glimpse into that kind of world.

It breaks the fourth wall of YouTube in a way because it shows you in business mode.
It shows me, like, turning on, turning off. Uploading, every aspect of it.

Photo: Laurel Golio

There's even a scene at your old high school where you write your Twitter handle on a whiteboard and joke, "See, always working."
It's part joke, but part not. That's just who I am. I'm in on the joke of that shameless self-promotion type of internet culture, a borderline-narcissistic YouTube person. That's why I'll sign things @TylerOakley. Even in group docs with my friends, I put @TylerOakley.

At VidCon, we also see you visibly irritated with one aspect of fame: the expectation to give every fan a personal experience in the least impersonal setting.
That was a really hard thing to include because, obviously, it's a less-than-flattering moment. I was processing everything as it was happening, but also had to be very conscious that I was in public. And then, also, there's a camera filming a documentary about me, capturing my emotions as it's happening. It's frustrating. In that moment, it felt like I was giving, giving, giving. It felt like, were there boundaries of what was enough? The line had finished, but there were still questions of "Will you do this, and will you also do that?" And I just need to make sure that I'm taking care of myself, especially during a weekend that is 100 percent the hardest weekend of every YouTuber's year. It's so emotionally demanding. I'm always trying to remind myself to have clear boundaries of when to take care of myself and when to go back to my room and just sit for a minute.

Did you ever ask the director to turn the cameras off?
No! There were some moments during the doc where it was like, "Do we gotta film this?" But I was really glad that they did, because even during the moment where I was annoyed or frustrated, being able to see it months and months later, it was like, it happens. If I wanted to show only the good, that's just a vlog on a YouTube channel.

Do you think YouTubers unfairly experience the Kardashian stigma? Famous for being famous.
If I'm stuck in the same pile as Kim Kardashian, I am happy. Kim Kardashian is a businesswoman, she is a philanthropist, she is a boss, she is a million things that a million people will try to say she's not. I respect how hard she works and cares for the people around her, so if people lump me into the same category as her, that's not the worst comparison in the world.

Last year, Forbes ranked the wealthiest YouTubers for the first time. Are YouTubers finally getting respect?
Well, I don't like respect being associated with income. The first question a lot of people might ask is, "How much do you make from it?" And judging by that answer, they'll give it the time of day. For me, it started as a hobby so I've loved it before you could make money from it. There are so many YouTubers who might not make any money who are incredible entertainers or filmmakers. So I think it's dangerous to equate income with worth, especially in a society that doesn't pay teachers. It's great to examine and report on the industry, but I want to always be careful and conscious of the ways we evaluate success.

Can YouTube ever genuinely rival traditional TV?
One hundred percent. My nephew watches YouTube on an iPad every time I'm home. Some of my friends get more views on a daily vlog than some season finales of TV shows, so when I think, "Is YouTube a rival to TV?" it's a no-brainer. Duh, yes, 100 percent it has been. Just look at how a lot of TV shows are now placing so much weight in digital content. So much of it is creating these packages that can also be YouTube videos.

How did The Amazing Race get you to make a reverse leap from digital to traditional?
The most enticing thing a show can present is something that I would never be able to do on my own. The reason I wanted to do The Amazing Race was because it was a chance to unplug, see the world, see other cultures, and experience these challenges that I don't think I could ever schedule or do had it not come to me in this way. We're seeing tons of different platforms be approached by these digital creators, and for the first time, those platforms are being welcoming and saying, "Yes, come, join us, try it."

Do you see yourself ever outgrowing YouTube?
I've always said I'll do it until I hate it. And I still like it, so that's a good thing. [Laughs.] If down the line I'm still doing it when I get married and when I have kids, who knows, I don't know. I don't wanna say no to it, but I don't wanna ever lock myself in that box and throw away the key. I'll do what I wanna do as I do it.

This interview has been edited and condensed.