Shanghai Surprise

This romantic comedy stars Sean Penn and his then-new-wife Madonna and was produced by none other than Beatle George Harrison’s production company. Harrison even appears in the film in a cameo role as a nightclub singer, in addition to performing songs on the movie’s soundtrack. But this couldn’t save Shangahi Surprise, which has a staggering IMDb rating of 2.7/10. The film is basically an old-fashioned romantic adventure/comedy, but a thorough (and deserved) critical drumming made it the Gigli of its day.

Pauly Shore Is Dead

OK, so Sean Penn’s appearance in this wishfully titled comedy is only a cameo. But it’s right there on his IMDb page, along with stuff like Casualties of War and Fair Game. Written, produced, directed and funded by, and starring Pauly Shore, the inside-showbiz satire has Shore faking his own death in order to save his career. Unfortunately, it didn’t save the movie, which got a less-than-stellar response from audiences and critics.

Crackers

Director Louis Malle is one of the greatest directors of all time, but Crackers is not one of his best movies, despite having Sean Penn in the cast. Penn is joining Donald Sutherland, Wallace Shawn, and others in this Hollywood reworking of the Italian caper comedy Big Deal on Madonna Street. Might be a good idea to stick to the original in this case.

It’s All About Love

This movie, from director Thomas Vinterberg, is about the end of the world. More specifically, it’s about a guy and a girl who try to save their relationship right before the end of the world. If ever there was a time to make a relationship last, I guess that would be it. Even as bad Sean Penn movies go, It’s All About Love is a debacle – star Claire Danes is rumored to have burst into tears after she saw it, and they weren’t tears of joy.

Hurlyburly

Showbiz satire is almost never the way to make a blockbuster movie, but Hurlyburly is a flop even by those standards. Grossing a total of $1,798,862 (so far), the movie might be too underseen to even qualify as a flop. Sean Penn joined a cast of other heavyweights like Kevin Spacey and Meg Ryan to adapt the critically acclaimed play by David Rabe, but even they couldn’t save it from oblivion. The movie is about people in the movie industry whose personal lives are more interesting than the schlock they produce, so maybe this was a case of art imitating life.

I Am Sam

This is undoubtedly the most well-liked (and well-attended) Sean Penn movie on the list, but critics have not been kind to it. And although I Am Sam was the inspiration for a lot of jokes and parodies when it came out, I don’t hear a lot of people talking about it today, unlike other Sean Penn movies like Dead Man Walking or Carlito’s Way. It’s not a terrible movie, but most people agree that the sentimentality of the plot is enough to drive them away. Still, it did inspire Robert Downey Jr.‘s classic “full retard” speech in Tropic Thunder. For that, I thank you, Sean Penn.