[SOME SITES BELOW MAY POTENTIALLY CONTAIN NSFW SUBJECT MATTER OR MATERAL. I AM NOT RESPONSIBLE FOR WHATEVER MAY OFFEND YOUR BRAIN AND/OR PERMANENTLY SEAR ITSELF INTO YOUR RETINAS.]

GAMING/ABANDONWARE SITES

[MyAbandonware] - Archive of tons of abandonware games.
[OldGamesDownload] - Another abandonware site.
[VETUSWARE] - Software and games for DOS, OS/2, AmigaOS and Windows 3.1.
[RGB Classic DOS Games] - DOS shareware, freeware, ware-ware and every-ware in between.
[Soggi] - An old site containing useful patches for various classic PC games.
[Patches Scrolls] - Another site for patches based out of Germany. Been using it for a few years now.
[Vimm's Lair] - A sizable archive of games from various consoles.
[Legends World] - Another fantastic site with downloads for tons of classic games spanning mutliple genres.
[FantasyAnime] - A great site for various RPGs, anime and anime-related games. Also contains a directory of various emulators for multiple systems.
[Game Copy World] - Useful directory for no-CD cracks and whatnot for countless games. Keep uBlock or AdBlock on or else you'll get flooded with shitty porn ads.
[The ROM Depot] - Sizable collection of roms and ISOs for various systems.

TECH NEWS

[Slashdot] - One of the oldest tech news sites still around today.
[Y-Combinator] - Up-to-date tech and hacking news aggregator.

ACADEMIA AND LITERATURE

[Sci-Hub] - Massive directory of free academic/scientific resources.
[Library Genesis] - Has a large collection of e-books ranging an array of topics.
[Archive.org] - Although the comparision is a little cliche, this is the digital Library of Alexandria: Contains a wide assortment of just about any form of media under the sun from literature, movies, music, etc.
[Project Gutenberg] - A massive archive of over 70,000 ebooks covering a wide assortment of topics.

FILE-SHARING/HOSTING

[Litterbox] - Temporary file-hosting site. Files can be hosted for up to a maximum of 3 days.
[PixelDrain] - Permenent private file-hosting.
[Catbox.moe] - Private file-sharing domain. Useful for Neocities file hosting.

VPNS (VIRTUAL PRIVATE NETWORKS) (INSERT SPONSOR JOKE HERE)

[Private Internet Access] - A decent VPN with open-source software available on Github.
[AirVPN] - VPN owned and operated by pro-privacy and anti-censorship activists that uses OpenVPN and WireGuard.
[TorGuard] - Pretty decent anonymous VPN. Used it myself for a long while.
[HideMyAss] - Another decently cheap VPN that costs about $4.99 a month.
[Mullvad] - Cheap VPN that also has it's own secure browser.

ALTERNATE SOCIAL MEDIA

[Fediverse] - A collection of truly decentralized, self-hostable and free social media alternatives.
[Spacehey!] - A fully-functional clone of MySpace in [YEAR_HERE!]?! WOW!

UNCATEGORIZED/MISC. THINGS

[The-Eye.eu] - Assorted files and reading materials.
[Textfiles.com] - Directory of various old text files and BBS boards. Anarchy and virus files are fun to look through.
[ProgArchives] - Massive resource for progressive music and its various sub-genres.
[The Index] - Directory of sites to watch that new-fangled Javanese animu or read them mangoes for free. (CONTAINS NSFW CONTENT)
[Tox/qTox] - Private peer-to-peer encrypted instant messaging application. (Personally, I'd suggest Toxygen for PC and aTox for Android.)
[The Old Net] - Surf the old-school internet the way it was back before it became a corporate shithole. YOU'RE GOING SURFING ON THE INTERNET-
[New Temple of The Screaming Electron] - An eccentric and esoteric BBS turned forum dating all the way back to 1989.
[Something Awful] - PURCHASE AN ACCOUNT.
[Church of The Sub-Genius] - A 100% legitimate religion who follows the wisdom and teachings of the great J.R "Bob" Dobbs.
[Narrat Game Engine] - Disco Elysium-inspired visual novel engine.
[Delisted Games] - A site for documenting various games that are being delisted or removed from digital storefronts as a result of corpo-fuckery.
[Interstate '76] - Fansite for the game Interstate '76 and it's sequels/spinoffs.
[Untamed Heart] - Klonoa fansite and forum.
[Heaven Games] - Another older website I used to frequent years ago for AoE2 mods. Also has tons of other sites for other RTS games as well.
[Keygenmusic.tk] - Remember the keygens you used to snag off Limewire, Kazaa or some shady site back in the day? They had some cool as fuck music and you can listen to the tracks they used here.
[Gateworld] - A Stargate forum and fansite. Perfect for the P90 lovers out there.
[Solatorobo Official Site] - Exactly what it says on the tin: The original website for Solatorobo: Red The Hunter preserved in all of it's 2010/2011 glory! (Requires Ruffle for Flash) (Site will be defunct next year so I may or may not be planning to snag the site to keep the original flash files preserved, stay tuned for info on that.)
[Killed By Google] - A site documenting the various pieces of hardware, applets and software killed by Google for seemingly no reason.
[Encyclopedia Metallum] - A fucking huge directory documenting various metal bands by genre and country of origin.
[Total Annihilation Universe] - A resource for Total Annihilation and Total Annihilation: Kingdoms.
[Sarna] - A massive resource for Battletech and Mechwarrior content.
[Wakaliwood] - DA WORLD FAMOUS DIRECTORS OF DA WORLD-RENOWNED FILM "WHO KILLED CAPTAIN ALEX".