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Richard Lockwood (Robert Pralgo)
We loved him because: As the mayor of Mystic Falls and the resident "full-grown alpha male douchebag," according to Alaric, the real purpose of the Mayor was to help us understand why Tyler was just so ... Tyler. Normally we love a man who hides floppy disks under his floorboards, but Mayor Lockwood had very few redeeming qualities.
We lost him because: While the Mayor hadn't triggered the Lockwood werewolf curse, he definitely carried on the bloodline, so he was affected by the Gilbert device in the Season 1 finale and assumed to be a vampire. He was ultimately killed by Charlie, a tomb vampire.