Plot summary from its Wikipedia entry:
Kiss Me, Stupid is a 1964 American comedy film directed by Billy Wilder and starring Kim Novak and Dean Martin. Martin plays a nightmare version of himself called "Dino," Novak portrays a trailer-trash prostitute, and Ray Walston took over a role originally intended for Peter Sellers as a jealous husband after Sellers suffered a heart attack. Excoriated by critics as being immoral upon its release, it has proven to be a prescient forerunner of films in which performers play unflattering versions of themselves, and includes one of Dean Martin's most fascinating performances. Ira Gershwin wrote the lyrics for the intentionally bad songs composed by Walston's hapless character.
The wedded couple characters played by Walston and Felicia Farr end up having sex with other people (Kim Novak and Dean Martin respectively), manage to shrug it off, and get back together. Such adulterous behavior on film upset Roman Catholic Church officials; the Vatican's Legion of Decency banned the film at the time it was released. However, by modern "anything goes" standards, the film is quite tame and has become a charming sex-farce with the passage of time. It also provides a rare glimpse into the personal life of Dean Martin. The film's opening scenes were shot during a live Martin performance at the late Sands Casino in Las Vegas. Also, the customized Italian Ghia sports car driven by Martin in the film was the performer's own real-life automobile.
The first four or five minutes (lasting for the duration of the opening credits) are without a doubt the best the film has to offer, and it features a great (practically historic) sequence of Dean Martin (playing "Dean Martin") as his "character" ends an engagement at the Sands Hotel Copa Room. So basically, you've got Dean Martin playing Dean Martin playing Dean Martin playing Dean Martin(?):
love that neon!!
The shots of Martin driving his own Ghia sports car down Fremont Street, and then out in the Nevada desert (presumably) are priceless. I was a bit stunned by the "What's the matter? That Sinatra kid missin' again?" line. The kidnapping of Frank Sinatra Jr. had a serious and profound impact on Frank Sinatra and is said to have aged him over night. So it seems unnecessarily tasteless and crude. It makes me wonder if Billy Wilder didn't have some sort of personal animosity towards or a grudge against Sinatra. But that's beside the point. Otherwise, this is a great sequence: