Wikipedia has a list of the Billboard No. 1 singles from the Hot 100 era, 1958 to present, which you can use. Your story can include up to seven song titles. Entries will be judged on cleverness, naturalness of reading, memorableness of the songs and overall elegance. You can send up to three entries and the best one, based on Will's opinion, will play the puzzle on the air in two weeks.
A: Winning entry: Thrift Shop! / What Goes Around Comes Around. / Rag Doll, / Good Luck Charm, / Itsy Bitsy Teenie Weenie Yellow Polkadot Bikini, / It's All In The Game. / I Still Haven't Found What I'm Looking For!
Runner up: Sugar, Sugar / I Heard It Through the Grapevine / (You're) Having My Baby / I Gotta Feeling / It Wasn't Me / The Stripper