What Movie Did Madonna and Sean Penn Star in Together?

Madonna and Sean Penn are two of the biggest names in Hollywood, and it’s not uncommon for fans to wonder if the two ever shared the screen together. The answer is yes! Madonna and Sean Penn starred in a film together called “Shanghai Surprise” back in 1986.

The Plot of “Shanghai Surprise”

“Shanghai Surprise” is a comedy-adventure film set in 1930s Shanghai. It tells the story of Gloria Tatlock (Madonna), a missionary nurse who seeks out a cure for opium addiction. Along her journey, she meets a fortune hunter named Glendon Wasey (Sean Penn), who convinces her to help him find some stolen opium in exchange for money.

The Reception of “Shanghai Surprise”

Despite having two major stars as its lead, “Shanghai Surprise” was not well-received by critics or audiences. In fact, it was widely considered one of the worst films of 1986. The film’s poor box office performance led to Madonna being awarded a Golden Raspberry Award for Worst Actress.

Fun Fact:

“Shanghai Surprise” was directed by Jim Goddard and produced by George Harrison, who also wrote and performed songs for the film’s soundtrack.


Although “Shanghai Surprise” may not have been the hit movie that fans were hoping for from Madonna and Sean Penn, it still remains as an interesting piece of Hollywood history. If you’re curious to see these two stars share the screen together, be sure to check out this comedy-adventure film from 1986.