I don’t want to over-recommend this movie — it is good not great — but it is certainly enjoyable to watch. It works because Owen Wilson self-consciously imitating Woody Allen, down to his shuffle and shoulder shrugs, is so absurd that it deflates the rest of the film down to the appropriately non-pretentious level, whether intentionally or not.
More importantly, the movie serves up some conceptual social science. It focuses on why we so commonly overrate the cultures of previous eras and see them as golden ages. It also asks the following question: if we somehow managed to meet the cultural titans of previous eras, how many of them would come across as blowhard hacks, if only because their own subsequent work has made their personae obsolete? Gertrude Stein and Man Ray are the most impressive characters in the movie, even though (perhaps because?) they are the least well known of the figures paraded across the screen. Hemingway and Picasso sink like stones and the viewer suddenly realizes that Allen sees Hemingway as his foil figure on issues of bravery and death. He cannot be allowed to look like anything but a blathering fool. (My view is that artistic creativity is sufficiently g-loaded that none of these people would seem anything less than extraordinarily impressive.)
Once again, this movie is Woody Allen wondering what other people think about him. Ultimately the point of view of the main character and the director/moviemaker are the same. You cannot say that about Larry David and that is why these superficially similar figures are very different and ought never to collaborate.