2. Bill Cosby
Technically, Bill Cosby botched his second attempt at a film career... Bill Cosby is frequently mentioned alongside the likes of George Carlin and Richard Pryor on the list of the all-time great comedians. And though he came away from the stand-up circuit strong with a slew of crime capers co-starring (and sometimes directed by) the incomparable Sidney Poitier, Cosby took a break from making films to create one of the most beloved sitcoms of all time, The Cosby Show. But to stay busy, Cosby would periodically take time to star in a feature film. His film credits swiftly devolved into a series of kooky comedy premises aimed at the same audience who watched his show. In Leonard Part 6, he was a secret agent who rode around on an ostrich. In Ghost Dad, he's killed by a devil-worshipping cabbie and comes back as a spirit to learn a very important lesson a la A Christmas Carol. It was likely due to the ridiculous and fantastic nature of these premises that his movies during this time period massively underperformed at the box office.