2. Robert De Niro – The Adventures of Rocky and Bullwinkle (2000)

Robert De Niro is one of the most prolific actors of all time, starring in true classics of both the crime and drama genres.

De Niro has also turned his hand to comedy in recent years, playing upon the reputation he built in movies like Goodfellas, Casino and The Godfather Part II in order to subvert audience expectations and bring a subtle, meta form of comedy to his roles.

De Niro’s role in 2000’s The Adventures of Rocky and Bullwinkle was something else entirely, though.

Playing the villainous “Fearsome Leader”, the acclaimed actor donned a monocle and a vaguely offensive Eastern European accent while trying his hand at a cartoonish, family-friendly action adventure based on the 1960s cartoon of the same name.

It was a strange departure from De Niro’s more traditional fare, and he seemed conspicuously out of place as the comedic villain. He’s mostly steered clear of sillier roles since, instead wringing comedy from his seriousness – indicating that he learned a valuable lesson from his part in The Adventures of Rocky and Bullwinkle.