Vintage gaming community.
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I'm pretty sure Doom will be the most popular (and my pick too), but I'll throw a shout-out to Epic Pinball; that Android table was the best one in the game anyway.
It's a simple choice, really, considering how many hours I managed to invest as a kid:
Commander Keen!
Jumping around with the pogo stick in Keen 6 was so much fun. I recently found the full game. Was surprised how hard that factory level was. But the music was still how I remembered it.
Probably Rise of the Triad.
Pretty sure I even bought the full game and never ended up getting very far. I also remember spending a little chunk of time on Hugo 3: Jungle of Doom, but could never figure it out enough to progress very far.
Edit: Another one I was trying to recall, the name was H.U.R.L.
Loved the Hugo games. The jungle one was probably my favorite up to the point where I needed to find out some trivia question about the name of some person's dog before the time of Internet.
I spent more time with Police Quest, which was similar. I remember trying the Hugo Jungle Shareware multiple times and getting frustrated going back-and-forth, stuck.
To me, it was Raptor Call of Shadows, a very nice shmup where you could buy new weapons between missions
ITT: everyone had the same “500 games on two CDs!” Shareware compilation CDs that I had growing up.
Or we are old enough to remember them the first time around vs reruns.
I'll show you mine if you show me yours:
Quake was awesome, especially since you could play the online multiplayer from the free version.
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)
Heretic was more than a Doom clone, it was developed using a modified Doom engine with the participation of Doom developers. It was a clever game in its own right, adding a lot of fresh elements to the then-budding FPS genre.
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!
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.
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.
I've been playing some Jazz Jackrabbit and Duke Nukem 1, they are both great. I think I prefer the design of DOS games to the design of console games.
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.
Was It shareware? Didn't know it!
I'm still enjoying It with OpenTTD https://www.openttd.org/
The original Transport Tycoon was distributed as shareware, would have been 95 or 96 when I was playing it off a shareware disc.
Not sure if TTD got a shareware release too, but i got that one as a retail boxed version.
But for 94 or 95 if you didn’t have a shareware version then your game was pretty much doomed.
Jesus, that's a deep cut.