Allan (Woody Allen) is a film critic for a San Francisco magazine, and tonight he is watching Casablanca in a revival theatre, even though he's seen it countless times, but he loves the way it resolves itself and how downright cool Humphrey Bogart is in it, especially in the final scene. He wishes he could be like that, to the extent that he holds conversations with an imaginary Bogart (Jerry Lacy), which is the closest he gets to conversation now his wife Julie (Susan Anspach) has walked out on him. Will he find another woman?
Well, he might, but she may well be closer than he thinks, in this, the film adaptation of Allen's hit Broadway play, retaining the four main cast members to work the magic they had on stage, on the cinema screen. Which was only too appropriate, as the cineaste mood was well and truly indulged here as Allan notes how few times his actual life measures up to the life he sees in his favourite movies, the Bogart spirit being the emodiment of that. Yet there was more to this conceit than having some lonely guy with an imaginary friend.
As was often the case with Allen's work, the relationship between men and women was what rose up to be tackled head on, or as head on as you could get when the lead character is so hopeless around the opposite sex - you wonder how he ever managed to get married in the first place. He may be a whiner and a neurotic, but it was testament to the star and writer's powers and knack for humour that you're never completely going to give up on him as a lost cause, mainly due to the way the laughs emerge from his observations and bad luck, often both in conjunction: Allen was at the height of his comic ability in this film.
He had handed the directorial reins over to Herbert Ross, a wise move as it looked to have freed Allen the performer up to throw himself into his role in a way that he truly seemed comfortable with and which informed his screen method for the rest of his career. Well, as comfortable as someone like his critic character ever could come across, which in this case was awkward and hapless as he is painfully aware that his goal - to secure a romantic relationship with someone attractive who really understands him blah blah blah - will always be out of his reach when there are other men who will always be far more confident and far more adept at dealing with women.
But there is one lady in his life who he can actually have a sensible conversation with and she is Linda (Diane Keaton), the neglected wife of his business-obsessed best friend Dick (Tony Roberts). It is these two who encourage Allen to go out on blind dates which they arrange for him, leading to some truly hilarious sequences of humorous male inadequacy as he is so terrible at acting like a normal person around these prospective partners that they might as well run a mile from him the moment he tries (and fails) to impress them. All the while the "ghosts" of Julie and Bogart hold conversations with him nobody else can hear, and it looks as if he will be alone for the rest of his life, except... Actually, the ending implies he'll be alone whatever happens, but at least he's wiser and had a connection for a while. Needless to say, some of the references may seem in bad taste now, but Play It Again, Sam was so well performed and so funny that you could forgive them; dare I say this was Woody at his most romantic?