The earliest game I can remember playing was probably Urban X life. The game that got me started was some old ass game from newgrounds; can't recall which one.
Ren'Py because of the rollback feature and how smooth every game usually is. That being said, not the biggest fan of visual novels anymore; I prefer sandbox or RPG adult games at the moment.
Started watching anime when I was like 5 I think. Hard to pick a single one but the ones that came to mind right away are AnoHana and Legend of the Galactic Heroes. If I had to pick a recent anime I'd go with Edgerunners.
Majority of them are HTML games that you can play on your browser. The popular ones out right now are Love & Vice and The Company. Most of them are really bad however.
Dreams of Desire was probably one of the very first renpy games that I've played. The game was amazing at the time and I had high expectations of Lewdlab; Unfortunately his current game(Midnight Paradise) is not as good.
Slow burn games are amazing when written well; However, inept writers often write large bodies of filler content with menial pay-off much later down the line and chalk it up as filler which I find pretentious and just simply inferior in quality over short linear games.