Never Make A Movie With Your Significant Other

Wino(na) Forever

Olivia Wilde and Jason Sudekis make an adorable couple, Olivia being one of the most gorgeous women in Hollywood and Jason being very, very funny. Sadly, news that the pair are filming a movie together over the summer, Relanxious, likely does not bode well for their relationship. As you will see below, once a couple tries to work together, everything goes to sh*t quick it seems.

Madonna and Sean Penn (Shanghai Surprise) — Then newlyweds, M and SP decided to film this 1986 comedy for reasons that truly are unknown. Just take a look at this synopsis: “Glendon Wasey is a fortune hunter looking for a fast track out of China. Gloria Tatlock is a missionary nurse seeking the curing powers of opium for her patients. Fate sets them on a hectic, exotic, and even romantic quest for stolen drugs. But they are up against every thug and smuggler in Shangai.” Needless to say, the pair split just a few years later.
Madonna and Warren Beatty (Dick Tracy) — Clearly not one to learn from her mistakes, M actually campaigned for a role in this film based on the classic comic, but offered to work for scale so no one would think any nepotism was involved, seeing as her then boyfriend was the star and director. The pair sadly split shortly after the film’s release.
Madonna and Guy Ritchie (Swept Away) — This woman never learns.
Kate Winslet and Sam Mendes (Revolutionary Road) — One of the greatest actors and one of the greatest directors, it would seem like nothing could split these two up. They always seemed so happy and in love and then they finally decided to work together on this film, based on the classic American novel by Richard Yates. A year later they were separated.
Winona Ryder and Johnny Depp (Edward Scissorhands) — We miss this couple every single day of our lives.