Leonardo DiCaprio in Drag, Circa 1960? Yikes!

How fitting that I just mentioned him on my New Year’s Resolution post! I have shocking information that Leonardo DiCaprio once dressed in drag. Or did he?

A friend of mine, knowing my obsessive-since-I-was-14 crush on Mr. Leo, sent me this in hopes of causing me to drop my fancy.

This photo is an actual scan of Tumblr user lo-parksthecar‘s grandmother’s classmate, Judy Zipper, from a 1960 high school yearbook. The resemblance to DiCaprio is pretty weird. See the real deal below.

I’m unsure how I feel about this. I have witnessed DiCaprio’s breathtaking appearance in person several times (without having the guts to say hi, I shall add), declaring him “the most handsome man who ever lived.” In that case, I must also have a strong attraction to this young woman’s grandmother’s friend. Oh, the horror. I’m in The Twilight Zone.

4 Comments

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