3. Chuck - Ishtar (1987)
Ishtar is one of the most notorious big-budget flops in film history, and is often featured on worst movie ever lists. Its not quite that terrible, but its definitely not the underrated masterpiece Quentin Tarantino rates it as either. It's a horribly stilted comedy that tries to emulate the classic Bob Hope/Bing Crosby road movies, but Hoffman and co-star Warren Beatty dont have the chemistry to pull it off. They play a talentless singing duo who get caught up in a Cold War plot in Morocco, and the laughs fail to ensue. The movie tries to subvert expectations by having Beatty play the bumbler and Hoffman the ladies man, but in no version of reality is anybody going to buy that. Hoffman is clearly aiming for awkward laughs, but it just comes off plain awkward instead; just like the film. Ishtar gets points for trying to be unique, but the movie is still a sorry mess that drags Hoffman and Beatty down with it.