If I try to think of my “best” sessions, I just think of a friend who died whom I played games with more than anyone else in the past decade or so. One on one we often played Memoir '44 (I’ve never played that with anyone else, in fact). The campaign of Imperial Assault that he ran for a group of us is a highlight – he had all the minis, had painted everything up, had a Star Wars soundtrack playing, and the game itself was great (frequently going down to the wire), so we always looked forward eagerly to the next session. I remember getting over-confident early on and charging into battle to the dismay of the rest of my team who then had to bail me out when I completely failed to do the thing I’d thought I’d do with ease (I pretty much just ran the wrong way, swung at thin air, and then got completely pummelled). It’s not so much that the games were remarkable than that I miss my friend, but it was games that we bonded over, so those are my “best sessions”.
It’s easier to get specific about “worst sessions”.
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Anticipated games - #653 by Phil was the worst single game session I’ve ever had at a games con.
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A game of Settlers of Catan at work involving a colleague with the worst AP. He spent something like 10 minutes mathing out the best possible places to put his starting pieces, and then just crushed us. (During the set-up the preceding player had to go out and fetch their dinner, so they placed their pieces and then left us to get on with it. When he got back he could not believe that we were still waiting for the same person to make their first move as when he’d left.) Essentially he’d decided how to win the game on his own before it had started, and then we all played out that result.
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A game of Space Hulk: Death Angel (I typed Space Hunk and was sorely tempted to not correct it) with a friend and one of his friends, the latter of whom I never invited to play games ever again as a result. SH:DA is a tough co-op game and without good teamwork it’s very easy to lose, so we would figure things out together, agree on the plan, and… this one player would do something completely different. Every time. He was obviously entertaining himself and didn’t care in the slightest that it made the game take twice as long as it would have done otherwise (which would have already have been a long game) as we tried to adapt to his chaos and make new plans. I figured that even given a competitive game, a person like that would be just as likely to try to ruin the game for another player as they would be to try to win the game for themselves, so that was the one and only time I played a board game with him.