On this day August 29, 1986, the film “Shanghai Surprise,” directed by Jim Goddard and starring Sean Penn and Madonna, made its debut. Despite the high expectations surrounding the movie, given its $17 million budget and the star power of the then-married couple, it struggled at the box office, earning only $2.3 million. The film is often remembered more for the off-screen dynamics between Penn and Madonna than for its on-screen success, marking a notable moment in 1980s pop culture.