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Britney Spears may have just won this week's round of best celebrity throwback snaps — the singer posted a photo of herself striking a silly pose with Leonardo DiCaprio on Thursday, simply captioned, "#tbt." It's hard to tell when exactly the snap is from, but based on Britney's girlish glow and Leo's baby face (and Boston Red Sox cap), we're guessing early 2000s [2]. You have to wonder if the pop princess and future Oscar winner [3] knew what their futures would bring when they posed for this. Keep reading to see more of Britney's best pictures over the years [4].