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Vicki Donovan (Kayla Ewell)
We loved her because: Everybody loves a bad girl! Vicki was Matt's pill-popping older sister with a self-destructive streak a mile wide, and we loved the occasional sweet sibling moment they shared. While we can't figure out what she was doing with Tyler (he was bad news back then), we loved watching Jeremy slowly chip away at her shell. Plus, she got Damon drunkenly dancing with his shirt off. We've loved people for less.
We lost him because: Whereas Caroline's neurotic, control-freak personality made for a relatively smooth transition into vampirism, Vicki's tendency toward addiction, obsession, and recklessness made her the worst baby vamp ever. Her fun didn't last long before she went all fiending blood-junkie on us and got staked at a school event. But hey -- two years later, she's baaa-aaack!