In 1986 Madonna was at the height of her powers. She was also married to Sean Penn, and the two decided to appear in a movie together, “Shanghai Surprise.” Penn is an acting legend, but Madonna is not. She’s had numerous roles that have failed to impress movie-goers, but this one might have been her worst.
Despite the male lead being her real-life husband, their characters had zero chemistry, and critical fingers were pointed at Madonna. She won Worst Actress at the Razzies, and the movie as a whole was nominated for five more, as well as a Stinkers Bad Movie Award.
Ted Danson as Captain Fred Hamill in Saving Private Ryan
Few movies captured the harrowing nature of war, quite like “Saving Private Ryan.” The men who stormed the beaches on D-Day became known as the greatest generation thanks to their force of will, their courage, and their unwavering spirit. Among the principal actors, most excelled, but Ted Danson had a hard time getting past his history as a comedic actor, such as in the famous sitcom “Cheers.”
Being a tough guy is one thing, but it takes a special actor to be a hard-nosed captain in World War II, and despite Danson's acting skill, he just didn't have the right stuff.
Katherine Hepburn as Jade in Dragon Seed
In the 1940s, Hollywood mishandled racial issues very often. One of the most famous examples of this problem was the 1944 war drama “Dragon Seed,” which starred Katherine Hepburn as a Jade. Thanks to some makeup magic, Hepburn was actually pretty convincing, and her performance was good.
However, it's still another black mark on the long and difficult history of Hollywood getting things wrong. The movie ended up losing the studio money, but it wasn't all bad – Aline MacMahon was nominated for an Academy Award for Best Supporting Actress. For a movie set in China, however, there were far too few Chinese actors.
Nicolas Cage as Johnny Blaze in Ghost Rider
It's not perfect, but “Ghost Rider” certainly isn't the worst superhero movie ever, or even on this list. It's not even the worst thing Nicolas Cage has been in, but there's no denying he was the wrong man for the part.
It's certainly one of his more uninspiring performances, and as far as tortured souls go, Cage doesn't really fit the bill. One critic leveled at Cage: “Cage needs to produce something special next to make up for crimes against cinema.” Ghost Rider's most famous feature is his flaming skull, and this Ghost Rider just got burned big time.
Katie Holmes as Rachel Dawes in Batman Begins
Katie Holmes got big by playing a cute teen in “Dawson's Creek,” but making the transition to love interest for DC's biggest hero, Batman, didn't work out. Many people found her role in the first of three Christopher Nolan "Batman" films to be lacking and forgettable.
When Maggie Gyllenhaal took her place as the character for “The Dark Knight,” people either didn't notice or agreed with the choice. Many think that Nolan had her replaced, but it seems even Holmes thought she wasn't right – she was reportedly offered the role a second time and ended up turning it down.