My first game ever, was an outdated shooting airplane game called Raptor: Call of the Shadows, for Windows 3.1 or DOS...yeah, that old! It had pixelated graphics but it was surprisingly elegantly designed for an old game, both in the menus as well as the various stages. It basically had 4 main sectors with various sub-stages each, with increasing difficulty. The player was supposed to clear the stages in a way that earned the most credits, to buy better weapons, shields and bombs. Basically unless you grinded the early stages over and over, it was impossible to clear the entire first sector.
Unlike many modern games, Raptor was also glitchless, something I can't say for many of the latest games out there.
Overall it's a game with a high replay-value, and I still play it from time to time.