Great Singer, Terrible Actress

3. Who’s That Guy? Part I (circa 1986)

Ask any cinephile this and he’ll tell you that Sean Penn is the man who played the lead role in Dead Man Walking, the award-winning film by Tim Robbins. Sean Penn is also the man who directed Into the Wild, a hypnotically poetic adaptation of the book which chronicles the tragic case of Christopher McCandless. McCandless was a graduate from Emory University who died with his Thoreau-esque experiment of attempting to live off North America’s wilderness. Yet, for Sean Penn, the beginnings were not very promising. In the mid-‘80s he was Madonna’s troubled, lesser-known boyfriend/husband. Sean Penn even acted with his then massively successful wife in the 1986 turkey, Shanghai Surprise. But he made good of his modest beginnings in film; Madonna made bad.


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