At a time when LucasArts was cheerfully mocking rival developer Sierra's fondness for punishing players with game overs you could trigger at the drop of a hat, Sierra themselves seemed intent to double down. In Gabriel Knight: Sins of the Fathers, not only can the titular protagonist suffer a variety of gruesome fates if you so much as put a foot wrong, but there's a point where you can soft-lock the entire game by failing to pick up an easily missable single snake scale from a busy crime scene — and you won't even know you did anything wrong for several in-game days. I'm not 100% sure this wasn't an oversight on the part of the developers, but at the same time, that's exactly the sort of shit that Sierra liked to pull.
Despite these occasional acts of cruelty, this inaugural entry into the Gabriel Knight series was one of the first adult-oriented games I fell in love with as a kid, and remains my gold standard for good point-and-click adventures to this day. It has so many outstanding features: its pitch-dark mystery-horror-thriller plot; its evocative setting in early-90s New Orleans; its haunting MIDI soundtrack, which you can check out for yourself below:
Also worth highlighting is the phenomenal voice cast. The four leads are played by no less than Tim Curry, Mark Hamill, Michael Dorn, and Leah Remini; and the characters they portray are no less impressive. In particular, the deuteragonist, Grace, is deservedly remembered now as an early exemplar of well-rounded female characters in video games.
Grace was acerbic, loyal, modest, courageous, and easily the most intelligent character, without any of the usual trappings of exaggerated nerdiness or arrogance. Even though she did inevitably become Gabriel's love interest later in the series, it was never at the expense of her independence. You don't get the feeling that she's a guaranteed prize to be handed to Gabriel when he becomes good enough at hero-ing, as she consistently prioritises self-respect and the greater good over whatever that horny bastard has on his mind. In fact, nearly three decades later, I think there still aren't that many Grace Nakimuras in fiction, and I'm glad I had her there as a role model growing up.