Kael'Thas in Tempest Keep, due to longevity of the fight and so many phases. Brutalus in The Sunwell for pure DPS race. Heroic Lich King in Icecrown Citadel for DPS race and overall team coordination.
There are many others but these are the tops because they were the most rewarding and some of the most fun bosses.
As for Destiny? None. All easy. Hardest part is the incompetence of teammates and their general lack of situational awareness.
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Hogger all day bro. #tookpartofthelevel1hoggerraidin09
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Don't forget patchwerk from naxx, the ultimate dps check lol
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Never raided that far in Naxx 1.0, and he was laughable in 2.0 version. But Brutalus is heralded by many to be a far tougher race since you HAD to rotate drums and bloodlust/heroisms in every dps group, plus he was a healing race as well.
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"Tempest Keep was merely a setback!"