We catch up with Richard storming through the jungle, and immediately go into an extended flashback. According to Wikipedia (because I didn't see any official confirmation of this in the episode, although I might have just missed it and been too lazy to go back and rewatch it to catch such a useless detail), we are now in 1867, and Richard is living with his sick wife, Isabella. Isabella gives Richard her crucifix, saying they will be together forever, and Richard leaves to fetch the doctor from another town. He gets to the doctor's mansion, but the doctor is an asshole, and will neither come visit Isabella (because it's raining outside and apparently he's made of sugar) nor sell Richard the necessary medicine (as Richard is poor, and all he has is not enough). They struggle, and Richard accidentally kills the doctor. He returns home with the medicine that he took from the doctor's house, and finds that his wife has died.
Richard is thrown in jail, where we learn that he is learning English by reading the Bible, and that he is to be hanged. However, an Englishman arrives and buys Richard to be a slave in the New World. He is taken aboard the Black Rock (dun dun dun!). The Black Rock is caught in a storm, and we briefly see the island and the statue before the ship crashes into it, destroying the statue and somehow ending up in the middle of the jungle (this still wasn't explained, which was annoying, but it's Lost, so it's to be expected).
They wake up in the jungle, and the Englishman comes into the hold and starts killing the prisoners, conveniently leaving Richard for last. As he is about to kill Richard, the Smoke Monster shows up and kills everyone but Richard. The Smoke Monster disappears, leaving Richard chained up in the hold. He is there for several days, during which time his wife shows up, tries to free him, and then is apparently killed or taken by the Smoke Monster. Eventually the Man in Black (from the season 5 finale) shows up and frees Richard in exchange for Richard's allegiance.
The Man in Black tells Richard that they are indeed in hell, and that the Devil has Isabella. He gives him a familiar-looking knife, and gives him almost the same speech that Dogen gave Sayid: Richard must go to the Devil and kill him before the Devil can speak--if he lets the Devil speak, he has already lost. MIB reveals that he is the Smoke Monster, but it was the Devil who took Isabella before he could stop hiim. He says that the Devil betrayed him and took his body and his humanity.
Richard goes to the statue, which is now only a foot thanks to the Black Rock crashing into it. He is attacked by Jacob, who demands to know where he got the knife. Richard tells Jacob everything that MIB told him, and Jacob drags Richard into the ocean and holds him underwater, asking if Richard still thinks he's dead. Richard admits that he is alive and wants to stay that way, and Jacob sits down with him to drink some wine (what?). Jacob explains that he brought the Black Rock to the Island. He uses the wine bottle as an analogy, stating that the wine inside is darkness and evil, and the cork is the Island. The Island is the only thing keeping the evil where it belongs. The Man in Black believes that everyone is corruptible, because it is in their nature to be evil, and Jacob brings people to the Island to prove them wrong. However, everyone Jacob has brought to the Island is now dead, because Jacob is an idiot and just lets the people run free once they get to the Island, not giving them any direction whatsoever because he wants them to help themselves without him having to show them the way. Richard, who is less of an idiot than Jacob, immediately points out that if Jacob doesn't step in to help, the Man in Black will. Jacob realizes that he has been an idiot, and recruits Richard to help the people as his representative in exchange for eternal life.
Richard returns to the Man in Black, and gives him a white stone, saying it is from Jacob. The Man in Black tells him that if he ever changes his mind, the offer still stands. He gives Richard back his wife's crucifix, then disappears, and Richard buries the crucifix next to a stone bench that is inexplicably in the middle of the jungle.
Back in the present, Richard returns to the stone bench and digs up the crucifix, then starts yelling that he has changed his mind and asking if the offer still stands. Hurley shows up and reveals that the invisible person he has been talking to is, in fact, Isabella. Isabella tells Richard that it wasn't his fault that he died, and that he has suffered enough. She tells Hurley that Richard must top the Man in Black from leaving the Island, or they will all go to hell. Evil Locke is shown watching this exchange from a distance.
The episode ends back in 1867, with Jacob joining the Man in Black on a log. The Man in Black says he tried to have Jacob killed because he wants to leave the island, and Jacob says that even if he were successful, someone else would just take his place. He gives the Man in Black the wine bottle, saying that it's something to pass the time. Jacob leaves, and the Man in Black says he'll be seeing Jacob "sooner than you think," and smashes the wine bottle on a rock.
As I said, the episode felt anticlimactic. It was good, don't get me wrong, but I felt like Richard's story would somehow be more epic. Maybe it's that it was just his origin, and we didn't really get to see how he became the Richard that we know today. The present-day Richard is (or at least was) perpetually calm, mysterious, and confident, and we didn't really see any of that. It would have been interesting to see that metamorphosis. That said, Nester Carbonell did a fantastic job of portraying the various emotional states that Richard underwent throughout the episode. The guy may wear a ton of eyeliner, but he can certainly act.
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