Vanilla Sky (2001)

Strangest Movies We've Ever Seen Vanilla Sky
Paramount Pictures

Riding high off the success of their previous collaboration, the lovely Jerry Maguire, writer-director Cameron Crowe and star Tom Cruise could do almost anything they wanted — and opted to remake the fascinating 1997 Spanish film Abre Los Ojos (which translates as Open Your Eyes), and to do it with one of that film’s stars, Penelope Cruz.

Both are deliciously bold and strange films, but Vanilla Sky is especially daring, shifting from a complicated romance to serious sci-fi. We don’t want to give too much away, but this is a movie that finds room for a visual shoutout to a 1963 Bob Dylan album, a discussion of your favorite Beatle, and a song by one of those Beatles. It’s one of the strangest movies, but is also, oddly, a comfort watch.

It also features a very good Cameron Diaz and Kurt Russell.

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