Rollercoaster Tycoon 3.: Wild!
Wild in of itself is kind of the redheaded stepchild of the RCT3 expansions because of how awkward the whole animal raising aspect of the game is, but there's one level in particular that would generate endless salt:
Tiger fucking Forest.
Inexplicably, you have to turn a golf estate into a
fucking Panda farm. The kicker is that you have to generate a stupidly high amount of profit from selling Pandas and you don't get much by simply buying pandas, getting their health up, and then selling them. Nope, you gotta make those bastards pop out children and you need to make
profit, so you can't just buy endless pandas and then sell the kids, because you have to earn back the money spent on pandas in the first place.
Oh, but it gets
better. Pandas are also the
neediest high maintenance motherfuckers in the whole game when it comes to animals. Because you have to give them
just enough space to make them happy, because not happy pandas won't fuck.
And even when you finally DO get them to fuck, that's when the ultimate insult begins: the game requires you to wait THREE FUCKING IN-GAME YEARS for the kids to pop out. And there's a LOT that can go wrong in the mean time (when I played the level, I had a panda glitch into a tree and when I finally realized it and removed the tree, the fucking in-game PETA came in with a helicopter and stole the 'mistreated' Panda...and her unborn children. Thankfully my other panda gave birth to twins so I didn't have to wait a zillion hours all over again).
And that's not even getting into the
other ridiculous part of the level which is paying back a huge loan at 29.9% interest while also making ride profit milestones.
Just the thought of Phil trying to tackle that level amuses me, because even if
somehow, the chat is able to get Phil through the money management part, even if using the easy money cheat (name a guy John D Rockfeller, get a million bucks, and it's infinitely abuseable) to cheese the actual management portion, there's NO WAY to cheat at the Panda fucking. It's meticulously bullshit in trying to keep those Pandas happy long enough to sell their children and Phil would inevitably fuck it up due to it taking
over an hour at minimum to achieve panda babies.
Kings Quest V. I know it has faults but I really do like the game.
But think about it, it's slow, Cedric the owl can be annoying, and he would have a really tough time with the puzzles.
All in all, I think it would be a slam dunk.
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Oh,
God, KQV. The best part of that would be the silly DRM mechanic with the wall puzzle - which you can only solve if you have the information from the game manual.
Phil would never learn this so even if he got that far, he'd legitimately hit DRM and chat couldn't really help him at all. He'd also never get the best ending regardless because like everybody says, he can't remember for shit and the genie lamp is a blink-and-you-miss it puzzle.