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Esteban Winsmore Has Resuscitated Second Life Through Trolling

Everyone on the planet has forgotten about Second Life, except the furries, bronies, and fetishists who still use it to act out their weird fantasies. We spoke to a guy named Charlie who trolls these people.

The virtual mug of Esteban Winsmore: Second Life's most entertaining menace.

A decade after its launch, the online virtual world of Second Life (SL) has devolved into a realm where digital avatars engage in furry orgies, fraternize in cities where rape is allowed, and dodge flying penises.

For the most part, the world has forgotten about Second Life. While it’s unlikely that SL avatars will once again grace the cover of business magazines, the eccentric community is experiencing a renewed interest thanks to all-around genius trolls such as YouTube user Charlie Winsmore.


A friend of mine introduced me to Charlie’s videos a few weeks ago. As soon as I laid my eyes on his most popular character, Esteban Winsmore, I fell in love. I don’t remember if I was initially attracted to his freakish ears, his blank stare or the perfect comical pacing of his speech, but I knew he was the troll for me. What makes Esteban so special (aside from his dashing appearance) is the seemingly naive way he interacts with other users. Players tend to react poorly to Esteban’s social clumsiness and lack of seriousness with reactions so strong you could almost forget that SL is a simple game. Charlie’s videos depicting the adventures of Esteban have now garnered hundreds of thousands of views, landed him on Reddit’s highly coveted front page, and generated tons of fan art, including a fan song.

I recently called up Charlie and giggled my way through our conversation about what makes Esteban so hilarious, his newfound virtual fame, and the ethics of trolling people who decide to live their life online dressed up as ponies.

VICE: First off, I’m a big fan of the way Esteban looks. He’s so different from all the other super buff, hypersexualized male avatars in SL. How did you come up with that avatar?
Charlie: I just played with the shapes a lot because SL allows you to look extremely macho and masculine. I think it’s funny to have a character who’s very tiny and very innocent. I play him like a very naive guy, friendly yet strangely aggressive if you step to him the wrong way. He compliments the oversexualized world of SL very well in the way that he stands against it all.


Talking to you now, I realize that Esteban’s voice isn’t your real voice. How did you come up with it?
I think it’s a combination of people I grew up around. It’s so racially ambiguous too. People can never pinpoint where it’s from. They say it’s French, Indian… I think that’s one of the fun things about him. He’s very ambiguous in the way he looks and the way he sounds.

Out of all the bizarre worlds in SL, what’s your favorite place to visit?
I can’t go back to most of the places I used to love visiting. After I got popular, people started figuring out who I was and they started kicking me out of all the places I loved. There used to be this dance club called Bootylicious, where it was the more urban crowd of SL. But it was really just southern white males dressed up as African characters trying to speak in an urban vernacular but failing miserably. That place used to be my favourite but it died out. Of course there’s the place from Esteban episode one and two with the older dance club folks. I loved that place so much and I’m so hurt that I can never go back there.

You’ve been banned?
Yeah, most of the places in my videos I’ve been banned from. The place with the bronies for example. It kinda sucks that my “fame” has stopped me from revisiting my favourite places in Second Life.

Why do you think you’re so good at trolling?
I think it’s because I’m not aggressive. I’m not insulting. I try my best to adhere to the rules of their virtual world. But I have one foot in and one foot out. I will entertain their fantasy. I think people don’t feel guilty watching my videos because I’m not putting people down. I’m playing along and I’m having a good time.


Is there a group of people on SL that you find easier to troll?
I’d say old people and people from southern areas. Oftentimes they can be polite, but they can also be on the other side of the spectrum. There can be vile people who are clearly carrying a lot of hate and baggage into this virtual world and almost blow up at the sight of somebody who threatens the seriousness of the fantasy.

The Home Invasions of Esteban Winsmore (Episode Three)

It’s funny you say that. In "The Home Invasions of Esteban Winsmore (Episode Three)", there’s a guy who completely flips out at you. Do you find it insane that people are so entrenched in their virtual world that they’ll scream at you?
In some ways yes and in some ways no, because I know that the world sometimes isn’t a fair place. I know that Second Life holds some people who at their core are hurt, but in that particular case, I think that guy had some real issues. I never quite made someone that angry at me in a video game or in real life. I think SL has a lot of people like that who might be a little kooky.

Do you feel bad sometimes for people when they get really upset?
Absolutely. I’ve kinda battled with the ethics behind the videos. I started censoring names and whatnot. Even though it might seem like a stupid thing to a lot of people, this whole idea of digital escapism, I do understand and empathize with people. I mean, ultimately my videos are gonna cause a little bit of damage, but I’m doing my best to hide the people even though their voices and their in-game characters are there. Because at the heart of it, it’s still real. I do kinda put people in danger for the sake of humour. It’s a double-edged sword.


I assume your videos are only highlights of Esteban’s adventures, does your trolling ever fail?
Yes, a lot. It’s harder these days because people recognize me a lot in the game. People are very aware, they’re on guard about people like me because it’s so common, especially since videos like mine started coming out. It’s difficult. My videos make it seem as though I’m infallible as a troll but it’s really not that way.

Do people get excited or pissed off when they recognize you?
A lot of them get really excited. I think people like me a lot in SL, but if they don’t know who I am, occasionally they’ll get mad just because I represent a player based in a community that is very hated. But if they recognize me for who I am, a lot of the times they’ll get very excited. They’ll want to take screenshots with me.

Esteban Winsmore's Big Brony Adventure (Second Life Trolling).

Do you have other accounts where you play the game normally?
(Laughs) No. I don’t open the game unless it’s for my videos. I don’t think I will ever enjoy the game in that way.

Fair enough. After all this time, do you still get shocked by the stuff you come across on SL?
Yeah, it’s always the weird sexual stuff. There’s a subset of the player base that’s bringing in all their insecurities and bizarre fetishes. I go into houses all the time that have walls just plastered with gaping buttholes and weird images. It does kinda catch me off guard. But for the most part, I’m pretty much jaded to everything that’s going on because I’ve been doing it for so long. Sometimes I’ll record something that is completely bizarre but it will just seem completely normal to me, and I won’t think about using it in a video until I show it to somebody and they’ll be like: “That’s the weirdest thing I’ve ever seen. How are you not weirded out by that?” It’s just normal to me at this point.


Wow! Would you say that SL is fucking with your brain?
It’s probably changed my psyche. I’ll probably never be the same even when I’m done with this. It’s ok. It’s for the best.

Do you think your videos have helped bring back some interest in Second Life?
I think I’m by far the biggest thing going on in SL right now. I think I’ve reinvigorated the fan base, maybe in a negative way, because I’m bringing all these people who don’t intend on playing the game seriously. But I’ve had people message me and tell me that they’re addicted to SL because of my videos. I guess I’m a good and a bad thing for SL. But I think ultimately any publicity is better than no publicity.

Have you been surprised by some of the people that have reached out to you?
Yeah! People in the furry orgies in my videos will leave comments and claim that it’s them in the furry orgies, which really confuses me. I think if I were in their position, I would hate me… But people seem to really like that they’re seen no matter in what manner they’re portrayed.

Are you going to do more videos with Esteban or is he too well known at this point?
I think there’s always gonna be a core of SL players that are completely detached from the rest of the internet. They stick to their islands and pretend to be vampires. Those are the people I’m aching to find. I don’t think I’ll ever retire Esteban just because he’s kind of a part of me now and I can act as him so naturally. When I play other characters I wish I was playing Esteban, because he’s so much fun for me to play as. He’s near and dear to my heart.

I’m glad I’ll get to see more of his small, freakish face. Thanks. @smvoyer