The three main characters are based on characters from James Joyce's "Ulysses" (which in turn is based on Homer's "Odyssey"). Stephen is based on Stephen Daedalus, a restless young writer in two of Joyce's novels; in "The Brothers Bloom", Stephen plans their cons with a writer's flair. Bloom is based on Leopold Bloom, who is wandering around Dublin, trying to find himself and his way back to his wife. In The Brothers Bloom, Bloom is figuratively looking for himself, and ultimately finds his way to Penelope. In "The Odyssey", Penelope is Odysseus' wife who waits for him through all of his travels; likewise, here, Penelope awaits Bloom through his wanderings.

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