In Melee I only play or even have fun with Falco and Dr. Mario and previously Zelda/Sheik (yes, both of them, not just Sheik). In Brawl I can actually play well with Ike, Lucario, Olimar, Falco, Wolf, Ganondorf, Captain Falcon, Zelda, Pokemon Trainer, Snake, Zero Suit Samus, Toon Link, and DK.

Also, it sounds like you and I approach Olimar a little differently. Although I definitely use managing expectations to my advantage.

It would be a lot of pikmin tossing, a lot of grab attempts and aerial approaches. Oh, and I’ll share a fun Oli’ tip I used back in the day. It’s easy to take advantage of his smash wind up animations all looking similar. So, if someone is getting up off the edge, run to them and charge to smash forwards. Do that a few times through out the match, then switch it to an up smash. The wind up animation is near identical AND his up smash (especially if it’s with a purple pikmin queued up) will likely give them the Team Rocket treatment. So the other person will jump over you, thinking it’s a forward smash…but nope!

The only one I have more fun playing as is probably Ganondorf. He’s nearly rock bottom on the current listings, but he’s too fun. Dat up tilt.

And oo! You’re hypothetically on. Although I’m very confused about how a Olimar v Olimar match would go. That seems very confusing to me.

The more I look into it, the more the community has decided that his easy gimpability off the edge is no longer a crippling weakness. Aside from that, Olimar’s got everything going for him, from disjointed EVERYTHINGs to super armor.

Ethos, if Nintendo didn’t use soup cans for their internet infrastructure, I’d challenge you to an Olimar ditto match.

PS I heart Olimar.

Wayne Gretzky’s 3D Hockey (N64)
I hated this game. A “friend” screwed me over and received this instead of Golden Eye. I got even later but in the meantime I had this thing I had no interest in and the other games I had at the moment were SM64 and OoT which I had already played too much. I knew nothing about hockey and didn’t (still don’t) like sports games but I gave it a shot. I played it a ton. It was great to play with friends and have a lot of fond memories of it. Got really good at it too. I don’t think I’ve touched a sports game since outside of a few FIFA matches here and there with friends.

Gran Turismo 2 (PSX)
Outside of Mario Kart (which is sort of a racing and party game hybrid), I avoid racing games. GT2 was the only game I had available on a long vacation. Despite my initial disdain for it, it quickly grew on me. It looked fantastic, it completely blew me away at the time. It also had great music and tight controls. Though I only had a passing interest in cars, it was awesome to customize and drive the best cars in the world. I did everything that could be done in the game, and that’s a lot.I couldn’t wait to play GT3, but eventually that died down as well as my interest in racing games.

Golden Eye 64.
After I got even with my friend, I got was what righfully mine. Unlike the other two games, which I played begrudgingly in the beginning, I wanted this from the very start. It was an awesome game, so much to do and so many ways to do them in. The multiplayer was amazing and holds many hours of fun memories for me and my friends at the time. I was the asshole that used only proximity mines and relished the moment where my traps blew on my opponents’ faces when they were sure they had me (wow, I totally forgot about that).

Medal of Honor Frontline (GC)
Another game that I played because there wasn’t anything I wanted to play available. I poured a lot of hours into the single player mode, but what I remember the most were the matches I had with my brother. We had almost nothing in common, so it was a nice thing to have.

When I try to think of my fondest moments in gaming, usually an image of a 16bit JRPG, a few Zeldas or some games from the PSX-PS2 era pop up so actually sitting down and trying to remember fun games I usually don’t even think about was really interesting (and a little surprising).