Characters: Larry Gigli and Ricki
Movie: Gigli (2003)
Let's just get the obvious out of the way. Gigli is a terrible movie. Some even go so far as to call it the worst ever in the whole entire world, since the dawn of silent film. It won a Razzie title for winning so many Razzies. Even the chemistry between Bennifer, whose relationship began on set, was a big fail.
Perhaps that was intentional, as he played a hard criminal with a gooey chocolate chip heart (...right) and she a lesbian—a full-fledged one with a girlfriend. Or maybe their lackluster attraction was caused by a whole lot of recurring pre-and post-date jitters. We'll never know.