The hacker lifestyle is a gonzo lifestyle, by definition.

We go out and do the weirdest shit just to see if we can. Cracking? Sure. Dumpster diving for parts? Absolutely. Building a HERF gun to see what it takes to make one? Probably not the best idea, to be honest, but sure. Taking over a hotel's television network to show My Little Pony on every internal channel? Let's do this.

It's easy to imagine Hunter S. Thompson as a hacker. He may not have been a hacker, but he definitely had the "Fuck it, let's do something weird!" thing down.