"Retro" is so big of a category now. But Final Fantasy IX was my least favorite. I have a feeling I'll get some hate for this but:

On PlayStation, the loading times were like 15-30 seconds before AND after each battle, the high random encounter frequency meant you would battle sometimes after every few steps, and monster variation was very low. And running never seemed to work.

So literally 10 seconds of movement, 25 seconds load into battle, battle one of the same 3-4 enemy groups in that area, 25 seconds load out of battle, and repeat.

The story was also very generic. Everyone seemed to love it, but it felt like they played every decision safe to create a nostalgia-friendly experience.

I played it so much but was always frustrated with it. Every time I see someone reminiscing about how great it is, I am just wondering what game they were playing.

Mavis Beacon Teaches Typing.

E.T. the Extra Terrestrial - Those fucking pits!

Any sort of point and click on a game console that only had a D-pad for controlling the pointer. I find them painful and unenjoyable.

Ocarina of Time. After the action and increasingly beautiful pixel art of the first four Zelda games, I found the 3D one boring and ugly.

Of course the TRUE least favorite would be some trash that never should have been pushed out, but if we're sticking with well known classics, I'm going with Castlevania 1-3.

The controls on those games were terrible. You were slow and clunky. Jumping between platforms required a trigonometric calculation. The weapons had a very specific and often a very strange path that

Enemies dipped in and out of attack range, and it constantly felt like I was supposed to press the attack button two seconds before the enemy was even on the screen.

I'm sure its not so bad once you memorize the levels and get used to the timing, but I have enough good games in my collection, that I don't need to waste my time adapting to the flaws of these games.

So I guess the obvious answer is some random shovelware 2600 game that barely works, so that's not much fun. In terms of games that have some traction and nostalgia, I can think of a couple that just don't do it for me. YMMV.

Contra is more of a beatdown than an enjoyable challenge, the konami code is iconic for a reason.

Defender is inscrutable and overambitious and the control are a weird early take on the side scrolling shooter.

Most arcade driving games were (and are) quarter eaters that aren't trying to do much that's interesting once you're behind the wheel.

Oh this is hard to think for. Because if the game was particularly bad I probably only played it a couple times and forgot about it.

Pretty much any sports or racing games without items (and fun haha).

Ah yes I remember one now. The Typing of the Dead

Myst.

Micky Mousecapade

I’m trying to think of something that was somewhat popular to make this more interesting. I’ll say Paperboy, I had a friend who really liked it but I never cared for it. Even when it showed up on emulators or retro game packs, it’s was always annoying and boring to me.

Dick Tracy suuuuuuucked.

Lots of “old” games i don’t like. But Retro implies Popular, so that narrows it down for me.

If I was to choose, it would be the genera of 3D Collectathons during the N64 and PS1 era. I don’t like the idea of being given a game with no direction and be told find your own fun. The N64 was filled with these games, like Mario 64, and Banjo Kazooie, the PS1 would be like Crash.

The exception to this rule was Spyro which gave the worlds a bit of a story after the first game. Enough to know what to do in a world, so when you stumble into the side distraction you can play them if you want. At times even those have stories.

Anything from LJN.

There are a bajillion crappy old games that I actually dislike more, but none of those would be interesting answers.

Of games that are generally well-regarded, so the gap between my opinion and the common opinion is largest, I'd have to say Final Fantasy Tactics.

It's not that I dislike it - it's just that, between FFT and Tactics Ogre, there are five games of the same type from the same devs and the same general era (FFT, FFT Advance, FFT A2, Tactics Ogre: Let Us Cling Together and Tactics Ogre: Knight of Lodis) and IMO, FFT is the bottom of the barrel - every single one of the others is better.

Pick any SHMUP. Even the classics like Raiden are the most boring, least engaging games ever.