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When Dennis Duffy, Liz's ex-boyfriend, becomes New York's latest local celebrity, Jack books him to appear on TGS. Dennis tries to win Liz back into his life. Meanwhile, Jack wants to find a young, hip Republican celebrity to appear at a John McCain fundraiser. Jack can only secure Bucky Bright, a TV star from the 1940s and 1950s. When Jack rejects him, he makes a friend in Kenneth, who happens to be a fan. Instead of Bucky, Jack tries to convince Tracy to become the celebrity face of the Republican Party.