Year: 2008
Britney and Marilyn share one glaring similarity: a life in the spotlight that highlights their troubles. Spears feels such an affinity towards the movie star that she requires a collection of Monroe’s DVDs at every hotel she goes to. In addition to emulating Monroe in the Esquire photoshoot above, she's also admitted to visiting Monroe’s grave in L.A. quite often. She even bought a plot near Monroe’s so she can rest by her for all eternity.

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