I can't tell you how many times I played the shareware version of Gazillionaire.
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I think this question just fried my brain. I don’t even know where to start.
Most played shareware of all time though was probably Transport Tycoon.
Might be pushing the limits of shareware, but the demo of Quake 1 on cd for a buck. A simple console command unlocked the full version.
Tyrian
Jazz Jackrabbit, Jetpack, and Combat Tanks.
Colobot - don't think it was "shareware" but it absolutely came as a demo on ceebot.com (still hosted there today I believe). Literally THE game that got me into computer programming and whatnot.
Otherwise for actual shareware, I loved Jazz Jackrabbit 2, Crazy Gravity and The Worm (found it!)
I really wanted to play a couple shareware games called Jetpack Joyride, and Hot Chix n Gear Stix as a kid, but neither of them would play on my Windows XP netbook as they had a hard check for if you were on either Windows 95 or 98, even with compatibility mode.
Jazz Jackrabbit always crashed out on my 486 D: I wanted to play it so badly.
Want a fun piece of trivia? Epic Pinball launched Digital Extremes, the developer behind Warframe.
And is named Epic because of Epic (Mega)Games
I spent a lot of time playing Raptor: Call of the Shadows, a vertically-scrolling shooter with an upgrade system.
There was also Rise of the Triad, a pretty decent Doom-clone
Wolfenstein 3d, and commander Keen
Mordor 1 The Depths of Dejenol
still available from Decklins Demise
Its the game that got me into dungeon crawlers particularly Demise: Rise of the Ku'Tan, and the epxansions Ascension and Revenge of the Tavern Keeper
My first FPS and an excellent one. Sooo many hidden rooms and insane enemies.
Apogee was on fire during that whole era
We had to be memory experts back then. QEMM FTW!
I spent so many hours as a kid on my dad's Thinkpad playing Gravity Well. It came on one of those "50 Great Games" CDs or something like that. The goal is to claim all the planets in the system, which you do by simply landing on them, then building defenses against your opponents. It's so much fun because your ship has pretty realistic inertia and the planets have actual gravity wells. The AI opponents can be quite difficult and aggressive. Challenging and fun, with great sound effects for the time!
This screenshot is from an Internet Archive page for the game, but I'm pretty sure it's only the shareware version. I gotta check again when I get off work!
Edit: I'm 99% certain it's from this exact CD for anyone interested. I've never been able to find a full version unfortunately...
I forgot all about this game! My go-to strategy was to attack freighters from the other factions while they were in flight and force them to change sides. My space pirate empire was unstoppable!
Realmz
I played a lot of TetriNET and Subspace Continuum with my old online community. Great times.
More detail edit: TetriNET walked so Tetris 99 could run. Version 1 does not install on Windows anymore (but has a Linux version). Version 2 works, complete with its archaic user registration that asks for too many details.
Continuum is a large PvP arena Asteroids-like 2D space shooter. It's on Steam now. Starts tough to control and with a high skill ceiling, so be wary of the veterans. The Death Star Battle map is a blast with a big group. It feels like trying to speed through a narrow maze on bumper boats during a huge battle.
Pinball Fantasies, Raptor, Heretic
Doom, Wolf3d, Diablo, and Castle of the Winds
Oh my god.. epic pinball! I had completely forgotten about this!! Thanks for that hit of nostalgia =)