Illidan was pretty tough for tanks to learn + resist gear requirements.
Sunwell was just OMG hard pre-nerf, max consumables all the time. Obvi had to have good tank / healer but one slack dps and you had no chance on most bossss. One tank mishap or healer missing was death. Honestly I give wow a lot of shit and can't stand it now but cutting edge bc raiding was a lot of fun / challenging.
Vanilla AQ and naxx pretty tough too but never did that when it mattered. Time investment in vanilla/bc wow was less but actual difficulty was harder IMO.
*edit: archimonde good for some good guild drama/luls when someone died and screwed raid with a crater. Haha
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