PRIVATEER: ASCII SECTOR / Christian Knudsen / PC
Privateer: Ascii Sector gets the recommendation here more for concept, panache and impressive programming than that I actually personally had fun with it. But the caveat here is that I didn't really like the original Wing Commander: Privateer either, which this is a clever ASCII-ified remake of.
The original game was set in the universe of the popular Wing Commander series, but unlike the linear mission-based gameplay of the main series, Privateer cast you in the role of a Han Solo wanna-be with an old space junker and not much else to your name. You were free to roam the galaxy, ally with various factions and take on jobs from hunting pirates to delivering cargo, or just turn pirate yourself. You started out with a mostly neutral rep with the different forces in the galaxy, and the jobs you took and ships you fought with would raise and lower that reputation with the different factions (similar to the older Grand Theft Auto games.) It was basically the ultimate game for libertarian IT geeks with a sci-fi fascination.
The original game pretty much was limited to a series of space stations, and your ship cockpit. Ascii Sector replicates stations by having you control a little avatar from an overhead view in the style of the old game-maker ZZT, and flying in space resembles something like an ascii version of Star Control. The game retains the basic control setup of the original, however, and missions, characters, dialogue and ship abilities have been faithfully reproduced for the most part.
The problem I personally had with the original Privateer is that the Wing Commander control setup was already bordering on having too many buttons and commands to deal with, and then when you add in keeping track of factions, missions, cargo and et cetera, it just turned into too much of a pain in the butt for me to ever get into (plus, my old 486 at the time had a lot of trouble with games that wanted a lot of EMS memory like Origin's always did.) Perhaps the biggest weakness is that the game just sort of dumps you off with no real idea of what to do next, and while the free-form exploration ultimately ends up being a major strength, it makes for confusing going at first and the ASCII format here doesn't help that at all.
Still, even if you really aren't into these sorts of games, I recommend giving this one a look anyway, if only as an amazing programming effort and a testament to how much you can do with the most basic graphics. It's also available on Linux and Mac in addition to PC.