Most difficult game you've played on the N64

Of the ones I owned the first one to come to mind is Jet Force Gemini. Not that hard but it is long and I missed many collectibles.
A Rareware game that I don't hear mentioned as often. It has their typical sense of humour and a lot of ant-looking aliens being exploded to bits.

Turok 2: Seeds Of Evil. Awesome game. Also don't have it anymore.

Shadows of the Empire was crazy difficult after the first couple levels.

Donkey Kong 64 was a pretty tame game overall, until you actually tried to get through the last hour or so of the game. Requiring you to master two arcade classics, then overcome amped up versions of those older games, THEN requiring you to go through that crazy fuckin' gauntlet of a final boss fight? It was a god damned nutty game.

I think I only managed to finish that last boss fight a single time.

I never really got into those. They felt too unresponsive to me.

Shadows of the Empire all the way! I have mixed memories about that game. Sometimes, the bleak music and grey graphics were horrible. I remember the long levels like being stuck in some reality-bending nightmare.

As a kid, I got up to the Boba Fett fight before I started using cheats. After that, I needed cheats for almost every level.

The vehicle levels I could do without cheats just fine. The swoop level and the last level were fun. I feel like I miiiiiiight have beaten the sewer level and the cargo ship without cheats a few times. But Xizor's Palace? Fuck that place, man. Fuck it, fuck it, fuck it. Particularly that god damned boss. At least the cheats were interesting and fun.

Shadows of the Empire is actually an interesting beast. I feel like people overlook how weird it was. It was a Star Wars book which got:

1. Multiple editions of varying levels of abridgment, apparently to make the book accessible to younger kids.
2. A line of Kenner toys.
3. A soundtrack. A soundtrack for a book.
4. A tie in video game. A tie in video game that was a huge deal. For a book.

I honestly can't think of any other book with a tie in video game like this.

Unpopular opinion: Shadows of the Empire is a middling-quality Star Wars book. At best.

But LotR was already a classic when those games came out. There's also a game "based on" Dante's Inferno, but I wouldn't exactly call it a tie in product.

Shadows of the Empire the game actually came out slightly before the book officially released, both in December 1996.