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Season 2

There was a time, long ago now, where SiIvaGunner was supposed to end after the first season, what a world that would have been... Season 2 was conceieved as a brief return for the holidays, culminating with the Christmas Comeback Crisis and its 12 uploads spelling SNOWHALATION...
This obviously never happened as SiIva is still active, but still, to think it could've ended in late 2017 is wild to think about.

The Christmas Comeback Crisis

What is a figment?

This will be very important later, so let's get it out of the way here. Figments in the CCC are the physical manifestation of of a character as they exist in popular conciousness, sort of like a "platonic ideal". Native to SiIvaGunner's computer, figments can normally kill and harm eachother as much as they want. They never age, never suffer from illness, only shifting as collective consciousness around a character shifts. There's some metaphysical stuff in the Siiva lore that comes up later, but ultimately that's not important for right now. What matters, is that when brought to the real* world, (hereafter the Central Cannon Continuum or CCC), figments can now die, and immediately upon death, are forgotten.

Who is Wood Man?

Wood Man is a robot master from Mega Man 2, but for SiIvaGunner he's a virus on SiIvaGunner's computer made from ripping the shit game Mighty No. 9. Wood Man is meta aware, and responsible for properly crediting the channel contributors on albums (in universe these are chalked up as corruptions). His first appearances were technically in Season 1, but ultimately I think it's better to talk about him here, along with the CCC stuff.
Wood Man gains control of the SiIvaGunner channel shortly after SiIvaGunner goes to sleep in the rip Title Theme & Ending - 7 GRAND DAD, He uploads a bunch of shitty MIDI covers of video game music, before leaving to fight Mega Man. He later reappears in the CCC, as one of the secondary antagonists alongside LazyTown's Robbie Rotten.
Wood Man is capable of transporting himself and the channel through different universes, and on the 1 year anniversary of the SiIvaGunner Reboot, shows us the genocide timeline, a timeline where Chad kills the Voice, and, we later find out, the rest of the world, replacing it with "Nice, Slick, Blackness".

The Christmas Comeback Crisis, for real this time

The CCC is a complex beast, that while starting out relatively simple as a parody of Kirby: Planet Robobot With SiIvaGunner memes, eventually morphs into a much, much more serious project... albeit still with SiIvaGunner memes. In Season 2, the CCC starts, with the Voice Inside Your Head taking over Grandiose City, bringing figments to the real world, capturing several notable channel memes, and attempting to kill all anime figments. Smol Nozomi, the last surviving member of the idol group from Love Live, which the Voice was unable to caputure, teams up with Meta Knight from Kirby and Santa in an attempt to defeat the Voice.
As this is happening, the Voice enlists the help of Wood Man, who eventually fucks off and does his own thing with Robbie Rotten of LazyTown, serving as the secondary antagonists for the series.

The Voice promises to help reunite Haltmann with his daughter, playing off of the plot of the game Kirby: Planet Robobot The Voice eventually produces Haruka doing a bad cosplay of Haltmann's daughter, leading Haltmann to betray the Voice by creating the Gadgetini Clone 2.0, making him flee his office. Haltmann then takes over the SiIvaGunner channel, attempting to sell it to the highest bidder. Haltmann becomes a major force in the lore as the de facto leader of Grandiose City, and the Voice is largely not present until Episode 10, where it's revealed he remains in the tower.

What about outside of the lore?

Season 2 is one of the most lore-heavy seasons, with most of the CCC coming out around here, several Haltmann's Archives, and a prevailing theme surrounding the CCC, antics of Wood Man, and generally just everything of that nature.
Season 2 was again, before my time, and when it wasn't based around the CCC, it was still covered with the same edgy content of Season 1 (though after the disaster that was 9/11 2016, most of this was religated to the second channel, Flustered Fernando.) This isn't to say that all of Season 2 was some sort of terrible mess, the rips increased in quality notably, and standards increased to new heights. It only took a year, and SiIvaGunner is finally making consistently good rips. Ultimately, aside from the occasional new meme, not much happened. At least, not until Season 3.