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Britney Spears and Leonardo DiCaprio Instagram Photo

Britney Spears Shares an Especially Nostalgic #TBT Snap With Leonardo DiCaprio

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. You have to wonder if the pop princess and future Oscar winner knew what their futures would bring when they posed for this. Keep reading to see more of Britney's best pictures over the years.

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