I would argue that the following camps are likely the suspects of replayability: Gameplay, depth, and Control.
Gameplay: Any game lives and dies by its gameplay, what is important in a timeless game, is not that it is executed flawlessly, but flawlessly in its own context, meaning that if a game has some gameplay issues, the game IS well aware, and gives explanation for it. You could argue that the Original Deus Ex did not have the best of gameplay, but within its own World, it made sense, and Thus the gameplay was quite alright. Something you could pass over because it simply fit. Old FF games, Mario games, the old Xcom games, system shock 2 and such illustrates fairly well. So gameplay that is good, but Works in context of own internal logic, Ironically the gameplay in those titles, have had better versions over the years, that either lacked the gameplay, but did not fit with those games own internal logic.
Add to that that most of those games were "firsts" of thier kind. Or of the first wave.
Depth: A shallow game is often easy to grasp and master, but in turn makes it pointless to play more then once, Depth is alot of Things, but usually it is the underlying systems under the Hood, Street Fighter 2 is still a blast to play, despite its gameplay being rather simplistic, but the depth of the systems, and precicion needed is what makes it. Again the Old X-com games are good examples, of depth, you had alot of Things to ballance at once, alot of systems you could perform well or bad at, any one you failed would not really hurt you, but failing a handful would. Games with depth does not automatically mean hundreds of sub menues or buttons used, but how well the mechanics are thought out, and the contexts of them. Games with Depth I would likely list as: Super Mario Bros., Mega Man, X-com, Baldues Gate, Some FF games, Counter Strike, Starcraft, UT, Fallout. Alot of Sim Building games (simcity, Theme Park, and such) show alot of depth and tend to get revisited by many I know.
It is easier to hav a kind of depth in MP games then in SP, but SP games do have the advantage of being timeless, where as MP games always depend on other players.
Control: Input control to be precise, how the game performs in accordence to your input, this might seem like an odd one, but really important. The old Mario Bros. games are games I consider to be near flawless in control input (well 1 and 3 by obvious reasons). I still enjoy playing them, same with Mega man, Fallout, Baldurs gate amongst others. How often do you go back to an old game, and find that they are unreasonably bad to play, with horrid responce, and janky controls? We rarely think about it when the game is new, we might consider it "part of the game" But as time goes on and the game is no longer new, we do observe more poros and cons to a game, and how it Controls is one of those very important Things. A game which has some bad control input, is almost unbearable. But I can still play Pac Man no problem (cabinet Pac Man in this case). This also Works for Pinball machines btw.
Added Bonus; Sound: Ok a 4th category I would like to bring up, Sound does not mean that the sound of the system have to be of high quality, but the sound that could be made often benefits greatly from being "great" within its own constraints (at the time) I will never speak an ill Word of most chiptune music and sounds of the NES. Alot of really Iconic music pieces and sound effects ar edeceptively simple, but they are all clean. Be is Half Life, System Shock 2, LoZ, Mario, Megaman, Street Fighter 2, Guardian Legend, Space Crusade (go to examples) All have sound that despite its age still sound great. I can argue though that there wer ea ton of games that had muddly jumbled music and sounds which back then, I did not think about, but now? I turn off the game within a few minutes ,because it grinds me.
Lastly something not specifically gamewise but: don't place a game to reflect the culture of the real World. Games that makes up thier own cultures, and not borrow heavily from pop culture, tends to age better, they are timeless in a sense, as they are not bound by the cultural real World settings at the time of make.
Ofcourse this is only my ideas, nothing of it might be true at all ;)
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