Concerning The Great Gatsby, one might consider Gatsby great because he loves purely and totally and completely.
This is his tragic flaw, if jargon usually reserved for tragedy can be applied to the novel. His love is idealistic and misguided, and ends up getting him killed, but it is poignant and is the driving force behind everything else Gatsby does. While Gatsby may well be the most miserable person in the novel because he does not have the object of his love, he may also be the happiest, because he does love as he does. The novel is first and foremost a love story, so one should look to love when examining the title.
Of course, Gatsby is also "great" in the sense that he started poor and has achieved the American Dream. And he's seen as somewhat of a circus attraction by people who frequent his lavish parties.
And there is another possibility, also. Some view the title as ironic. The "great" Gatsby achieves his wealth by illegal means, and is really nothing more than a love-sick grown up who never grew out of adolescence. This is a minority view, however.
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