Everquest. Admittedly for a long time the extremely strong community made the game bearable, but when world of warcraft came out, most of the people left and the quality of the game went right out the window. Put as blunt as possible,, EQ's main problem was that the gameplay was total shit. It seemed like the game designers were attempting to make everything as horribly difficult as possible. They probably were, considering EQ was originally intended to be a pay-per-hour model, not pay-per-month. Even so, some of the things that they did were, put simply, dick moves. For example:
In one of the starting zones(qeynos hills, intended for level 15-20 IIRC), there was a random spawn that was around level 40 and hostile to the players. Thus, when he popped, he would go on a killing spree where tons of people lost XP.
The Z axis NEVER worked right, and thus monsters could hit players up on a ledge while the player was unable to respond.
One of the later dungeons was completely underwater, and several monsters could dispel enduring breath.
In one of the freaking STARING CITIES there was a giant hole in the ground you could easily run into if you weren't careful. The hole led to a zone where levitation DIDN'T WORK and you would fall all the way down and DIE ON IMPACT! The only way you could get your corpse back was to have a high level necromancer summon it. I once spent FIVE HOURS trying to coordinate a summoning for a guildmate. That zone still pisses me off when I think about it.
Another one of the starting cities was built entirely above the ground. it was stupidly hard to navigate and while the fall wasn't automatically fatal, if you were low level and had no map, you would likely fall off a ledge and die. And since the zone typically looks almost exactly the same all the way through, it would be hard to find your corpse in one specific hill when all the hills look alike.
And so forth. Somehow, I played it for five years and got up to level 63 (out of 80 at the time) How I am not sure because leveling up was so freaking repetitive. To kill monsters, you typically "kite" which is when you increase your speed, reduce the enemies speed and run away firing damage spells at the enemy. While it was okay the first dozen levels or so, it soon turns into a grindfest when you have to do it thousands of times per level. I think the only way I stood it as long as I did was because I wasn't on my antipsychotic medication at the time. Yahtzee said "going for 100% completion is for unemployed psychotics and koreans" but I think that could be said for leveling up in EQ also.