"Kiss Me Stupid" is a minor movie by the great Billy Wilder. All of the great Wilder movies do not follow the standard three act structure. It is basically: Introduction, conflict, resolution. The viewer generally knows where the three act movie is going and how it is going to end. Wilder's "Avanti" follows this. It is a stock boy meets girl movie where the boy ends up with the girl. very dull from most film makers and very disappointing from Wilder.
"Kiss Me Stupid" shows promise since it does not fall into the three act structure. It seems to set up a very unusual conflict. Dean Martin character, whose image is loud hard drinking womanizing, is shown to be the opposite. He just wants to be left alone in quiet. Orville wants to sell a song to the Dean Martin character so he tries to appeal to the person he think Dean Martin is. The film opens up and could go anywhere. Narratively, it is interesting but the execution is flawed.
The main issue is the casting. The Orville character is written as highly jealous husband who frantic behavior get him in trouble. Unfortunately, the character is played by the laconic Ray Walston. Almost all of Walston roles have been cool and reserved. Frantic does not suit him. I spent the movie pondering what the movie could have been with someone like Jack Lemon.
The movie also drags in places. it is almost like it is missing some sort of sub plot which fill out the movie. Still it is an interesting failure.