Esteban Winsmore’s Best Moments

Be forewarned: this is NSFW.

It’s not often that trolling isn’t related to destructive or obstructive behavior, but you can’t talk about trolling in Second Life without discussing one of the “greats”, Esteban Winsmore. Now, I express only my opinion here, so don’t get up in arms, but the history behind this “character” is one worth telling. While many struggle with figuring out the elusive world of profitable business ideas in Second Life, this guy has pretty much forged revenue from being nothing short of obnoxious. Spoiler alert: I love his work.

Esteban is impossible to get an actual interview with, but let’s take a look at his history, which seemingly originated in July of 2010 on YouTube with “The Story Of Esteban Winsmore (Episode One)” where he decides to hit up the club scene, much to the dismay of club owners. The constant theme in his videos is simply his ability to find people that he can easily irritate to the point where they rage, despite the option to simply eject and ban being accessible to most. Short version- his trolling ends up being comedy gold.

He’s extended his reach beyond YouTube into Twitch (where he livestreams), Reddit and others. From a Second Life point of view, he’s a bit of a virtual celebrity. While some might question the ethics of his popularity, it’s hard to deny the muted genius behind his ability to prank the heck out of people. If people learned to lighten up, he wouldn’t have as much of an impact. But there’s always “that person” that probably rages over everything, and the results are glorious.

So today, in honor of Esteban Winsmore, here’s a list of his top 3 classic videos (in my opinion, and in no particular order).

1. The Home Invasions of Esteban Winsmore (Episode One)

A classic Esteban video, where somehow he ends up able to sit in people’s homes until they rage, rather than be logically booted.

“Bang bang skeet skeet, I’ll never leave”



2. Esteban Winsmore and Jesse Threebeards: Karaoke Kings

Esteban and Karaoke- it’s just ridiculously amazing. And that poor woman really tried to help.

3. Esteban Winsmore’s Big Furry Adventure (Second Life)

I can’t even caption this to do it justice. I do need to remind you it’s NSFW- YouTube took down the original video, if that’s any indication.


What are some of your favorite Esteban moments? I want to hear from you!

Bria Oceanside

ZoHa Islands Blogger/Social Media