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Charlie, after being told by Desmond that he is going to die, begins to recount the five highlights of his life - his "Greatest Hits" - by writing them on a piece of paper.
In a flashback, Charlie recalls the first time he heard "You All Everybody" on the radio. Drive Shaft were on their way to a gig in Clitheroe, Lancashire, and Charlie was ready to quit the band when the song came on the radio. He decided to stick with it after all. On the island, Charlie titles this highlight "#5: The first time I heard myself on the radio."
On the island, a group of survivors follows Jack into an open field. Jack says his excuse for acting strange lately is that he has been planning, with Juliet and Roussea, the impending counter-attack on the Others, who have vowed to steal the Losties' pregnant women.
In a flashback, Charlie reflects on learning to swim as a child. He titles this memory "#4: Dad teaching me to swim at Butlins."
Sayid confers with Jack and explains that the reason Naomi's satellite phone is not working is that Rousseau's distress signal is still going off. Also, there are some transmission-stifling signals coming from an underwater Dharma station called The Looking Glass.
Charlie talks with Naomi, and they reminisce about life in Manchester, where they are both from. Naomi tells Charlie that after his "death" aboard Oceanic 815, Drive Shaft enjoyed a career resurgence with a popular "Greatest Hits" album. This news pleases Charlie, but then he sees Desmond and is reminded of his fate - he is supposed to die. In Charlie's third flashback - which he titles "#3: The Christmas Liam gave me the ring" - Charlie's brother Liam gives Charlie an old family heirloom, a ring that belonged to their grandmother. Liam tells Charlie that he should hold on to this ring, since he will be the one to live past 30 and have a family.
Charlie is sitting with Claire when Desmond pulls him away. He has had another vision - it's of Claire and baby Aaron getting off the island. The catch is that for this flashback to become a reality, Charlie must die. In Desmond's vision, Charlie drowns.
On the beach, the survivors are planning their attack on the Others. Sayid says they need someone to swim down to the Looking Glass station to disarm the transmission-blocking signal. Charlie volunteers, although the consensus is that it is a suicide mission. Charlie figures this might be a way for Desmond's last vision to become real.
The survivors are laying down dynamite to blow up the Others when Karl suddenly arrives on the beach and tells them that they have their timeline wrong - the Others are coming to attack them tonight, not tomorrow. They rush into action. Jack is to lead a large group to the Radio Tower, while Jin, Bernard, and Sayid will stay behind and hide in the bushes with some firearms.
In a flashback, Charlie saves a woman being mugged outside the Covent Garden tube stop. He lists this memory as "#2: A woman outside Covent Garden calls me a hero." The woman happens to be Nadia, Sayid's long lost love.
After Charlie says his goodbyes to Claire and Hurley and more friends, he and Desmond take off in a rowboat to go out to the water above The Looking Glass. Desmond says that maybe he's got it all wrong about the flashes, and that maybe he should go in Charlie's place. Charlie knows he must do the task, and he knocks Desmond out with an oar and dives into the water. He leaves his list of "Greatest Hits" in Desmond's pocket.
In the final flashback moment, Charlie remembers the day he met Claire, in the wreckage of Oceanic Flight 815. They hit it off right away. Charlie jots this down on his sheet as "#1: The day I met you." Charlie swims up through a hole in the bottom of the Looking Glass station and begins to look for the button he is meant to push. Suddenly, 2 women burst out of a door and pull guns on Charlie.