I personally prefer all 4 Pirates films to Cutthroat Island but, since the critical consensus is that the Pirates sequels are flawed at best, I'll make it easier for myself and just suggest this: Pirates of the Caribbean: The Curse of the Black Pearl is better than Cutthroat Island.
-- Jack Sparrow is more fun than any character in Cutthroat Island.
-- Geoffrey Rush's Captain Barbossa is more fun than Frank Langella's Dawg.
-- Orlando Bloom and Keira Knightley, while quite wooden, share more chemistry than Matthew Modine and Geena Davis (who shared none).
-- The side-characters in Black Pearl are more interesting.
-- The supernatural elements of Pirates make the plot more interesting.
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