Exile Series
https://en.wikipedia.org/wiki/Exile_(1995_video_game_series)
http://www.spiderwebsoftware.com/exile3/exile3_shot1.html
This was a shareware series for Mac from the 90s. There's several games, Exile I: Escape from the Pitt, Exile II, Exile III, etc. I played them all but mostly Exile III. It's an RPG that is very much D&D. It features a top-down perspective and you control a party of heroes of various classes. There are items, quests, etc. and the game is MASSIVE in scale.
Subspace/Continuum
I can't believe this game is over 20 years old.
This is the first MMOG I ever played. I started in the 90s and played off and on for years. I remember in 2014 at some point, after I got out of prison, I checked it out again and found it to be dying. There were barely any players left in some of the servers. That said I'd run into people that were like "I've been playing since 2002!" and I'd feel old as fuck. It was amazing to me that people who started then considered themselves veterans of the game when I'd been playing since the 90s.
This game was one you could play with a slow Internet connection back in the day. It was also 100% free!
Basically you log-on to different servers. The servers have different games, style of play, etc, but the look is basically the same, as are the ships for the most part. For example, some of the servers are just about killing other players (and the weapon fire rate differs). Some are about controlling a certain area of the game. The best, however, were the "flag capture" games where you'd be divided into teams and capture little glowing orbs called "flags." The idea was to drop them off in one of several mazes on the board, hiding them and defending against the other teams attacks while also taking any of their flags. Capture them all and survive the timer and your team won.
I recently found out the game has experienced a revival via Steam, which is awesome.
Realmz
https://en.wikipedia.org/wiki/Realmz
Realmz is similar to Exile. Both were published by Fantasoft Released in 1994 for Mac a Windows version was released in 1999. It's a lot like the Forgotten Realms D&D module, so much so I think Fantasoft was contacted by TSR over it and Fantasoft had to make changes.
I remember when I first played the game I kept dying. The idea that I couldn't fight whatever I wanted without first leveling hadn't occurred to me yet.
Factory
An old Mac shareware game that is a strategy game. You basically run a factory, building products down an assembly line. The products change and it gets a lot more challenging as you progress with much more to the process. If you fail to meet your quota of finished products for the day, you lose.
Simple, but so much fun.
Universal Soldiers
This came out on the Genesis and is "based" on the Universal Soldiers movie... except it's not and thank God for that.
This game is fucking insane. It's like they shoved as much crazy shit as possible into it because they couldn't figure out how to make a game of of the movie otherwise. Wasps that attack you from nests? You can turn into a spiked ball at will? Don't remember that shit.
The game is FULL of crazy power ups including tons of insane fucking weapons. Oh and when you get them the game TELLS YOU WHAT THEY ARE (although I can't make out what the fuck it's saying). Also, there's a button combination that allows you to just go ape shit and turns the screen into chaos.
Oh and the soundtrack? Awesome.
Wiz N' Liz
Who are these people!?
Another Sega game. This game is beautifully weird. The music is beautiful and charming. The game play is fun. It has an interesting alchemy element where you mix fruits together to get things including unlocking some really weird/cool secrets and hidden mini-games. The bosses are weird and hilarious (i.e. The Freaky Flower) It is two player as well.
The graphics are gorgeous. They really set the mood and makes you feel like you're in a dream. The entire game is based at night.
The entire point of the game is you run through levels collecting rabbits and the rabbits product letters (and fruit and other things) and you collect the letters until you spell the word at the time. You have a time limit.
Dope Wars/Drug Wars
This game has been around since the 80s and there's a bunch of versions of this game now. One you can play here:
https://gamegraveyard.net/drugwars/
The Dope Wars version (pictured above) for Windows is the best, IMO.
You basically buy and sell drugs and travel from city to city and try not to get busted. You can buy weapons and fight back. The idea is that you buy one drug at a low price in one location and then travel to another place where it's at a high price and flip it.
Super fun and addictive... like drugs!
The Helicopter Game
http://www.play-helicopter-game.com/
You glide a helicopter through a green maze with the push of a button. This game is insanely addictive and has been around for years.
Pizza Rush
This game is so obscure I couldn't find a screen shot for it. Basically in a top down view you drive a car through a neighborhood delivering pizza and making money. The thing is, and this is slightly retarded, you can't hit any other cars and you can't go around them so if you see one coming you better turn or put it in reverse.
IndyCar Racing
https://www.youtube.com/watch?v=whDLSPkZg2k
1994 game released by Papyrus. The graphics in its day were epic. It was innovative in that it had instant replay.
There was also a mode where you wouldn't take damage. I used to turn and run head on into the other games and watch them break apart. The tires would just bounce on the track.
Burning Rubber
What makes this Mac shareware game fun is that you can go insanely fast and all kinds of shit comes at you, from other cars, to oil spills and cops chasing you. If you master the reflexes required to do well with this game it's extremely satisfying.
Jurassic Park: Operation Genesis
https://en.wikipedia.org/wiki/Jurassic_Park:_Operation_Genesis
Basically this is SimCity except you're building a new Jurassic Park. The game is awesome. One problem is that with the exception of the PC version (which is the ideal version because it's better and has fan made modifications) the console versions (PS2 & X-Box) are pretty expensive.
Rocket Knight Adventures
A side-scrolling platform game for Sega this is actually a pretty sought after game for collectors. The game play is fun, the soundtrack is good and the graphics are really beautiful.