The 1990 Punisher game for DOS is an impressively amibitious attempt to do a sandbox-style open world, years before Grand Theft Auto would make that a viable genre. Unfortunately, they forgot one of the cardinal rules; high concepts don't matter if your core gameplay isn't fun, and basically every bit of this game is a tedious clunkfest.
The setup is that the Punisher really really wants to kill the Kingpin, but in this version he moves between safehouses every few weeks rather than chillin' at the Fisk Industries tower. An informant is ready to give Punisher the location of the current safehouse for a cool $500,000, but Kingpin will only be there for 14 more days and the informant can't help after that. So we're off to raid as many criminals and collect as many bounties as quickly as possible to drum up the money.
The game plays out in real time, but the Punisher's punishing activites are restricted to the wee hours, so the game is broken up into individual days that start at midnight and basically go until you return to your warehouse base. Said activities are also only restricted to a chunk of Manhattan (where you would think street crime wouldn't be nearly as rampant, but hey). You can move freely through this map, both in your "battle van" and on foot. Microchip has one main mission for you each game day that nets you in the range of $30,000 - $50,000, but you can also pick up side missions as you go by listening to your police scanner.
The van is the main means of transportation, and while inside you're in a simple wireframe driving sim. It's handled by only allowing you to drive straight forward, though you can pull a u-turn at any time, and as you approach intersections you can use the < or > keys to make a turn. You'll see other cars pass you periodically, but most are just for graphical flavor and can't be interacted with, save for occasional "enemy cars" who basically do a drive-by to damage your van then disappear. When enemies appear you can toggle a machine gun on to shoot them before they shoot you, but if you shoot civilian cars a police chopper will nuke you from orbit.
Driving is hard to fail at, and you'll always get where you're going once you know all the required keyboard keys, but it's really tedious. The main problem is that the blocks are insanely long, requiring you to speed at the max of 150 MPH just to make travel manageable. But here's the problem -- the damage done by the periodic enemy drive-by cars gradually limits your top speed, and there's no way to repair it save going back to the warehouse and sacrificing a game day.
Going on foot is actually faster, as the two modes are two completely different maps and the "foot map" has much shorter blocks (plus no random enemies). The only issue with this is that you don't get the notifications as to what intersection you're at or what street address you're parked at, so you have to know exactly where you're going.
I could see the driving mode being worth putting up with if the gameplay outside the car was fun, but sadly it's as bad if not worse. The Punisher moves in choppy tile-based style like it's an old-school RPG, so there's really no strategy to gun battles save finding a wall to hide behind and waiting for enemies to walk around the corner. If you can't do that, you have to just gun it out with them in Shadowrun SNES style and you very quickly lose health against even the basic mooks. When the Punisher first walks onto a new screen he also gets deposited at totally random sides of it sometimes, leading to confusion as to where you are while you're getting shot up.
There's some sort of side-scrolling "scuba mode" in certain missions too apparently, but I never got far enough to encounter it. It seems to be a relatively small part of the game, so it clearly isn't gonna save anything.
I really wish this worked better as the core concept is great, but it's just not at all fun to play.
* Link to manual scan
(doesn't have keyboard commands though)
* Technical supplement
(this is where the keyboard commands are)