Oh my god.. epic pinball! I had completely forgotten about this!! Thanks for that hit of nostalgia =)
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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.
So many great titles in the comments. I'll add a few of mine:
Jill of the Jungle
Zaxxon
Heretic (Doom clone)
Stellar 7 (can't recall if shareware or if I just shared it)
I don't know if it was their SDK or what, but Epic's sound design in this era was so good. Jill of the Jungle still stands out to me for that.
All great selections!
I was a fan of all of the Apogee platformers:
Commander Keen,
Cosmo's Cosmic Adventure,
Monster Bash
Also Lucasfilm games:
Loom,
Maniac Mansion
What a great time for PC gaming!
It's a simple choice, really, considering how many hours I managed to invest as a kid:
Quake was awesome, especially since you could play the online multiplayer from the free version.
Quake
Scorched Earth
Realmz
I played a lot of 2 games that nobody I've spoken to has ever heard of: Mordor the depths of dejenol Exile escape from the pit Both were great, I think exile had been remade by the programmer with a different title too
There was a Mordor 2 shareware as well. The game never got a full release but laid the foundation for Demise: Rise of the Kutan (2000). The rights to the game were sold to Decklin and they released expansions Ascension (2016) and Revenge of the Tavern Keeper (2024). Demos for Demise and the expansions are available at https://www.decklinsdemise.com/
Found out the exile games are now distributed as freeware https://www.spiderwebsoftware.com/exile/winexile.html https://www.spiderwebsoftware.com/productsOld.html