I'd love to see Ross play The Day The World Broke, as he's the only youtuber I can think of who'd be able to preserve it properly! It's a game from my childhood that still holds up whenever I can get my copy running again, and while it has a few stinkers for bugs that (of course) can break the game completely, it's short enough that once you know the steps a playthrough can go fast. There's a great cast of characters and it's a good story.
Cheers!
(Also, it's on brand.)