Deconstructing Harry as great, it jumps to 1997), and thus it must follow, as night the day, that his next project after the bittersweet, playfully intelligent Midnight in Paris was not going to be that good. And in this respect, at least, To Rome with Love does not disappoint. It is not a great film; and especially not by the standards of an Allen film, though as with many of his late-career works, I think it's easy to be too hard on some of its faults (and, admittedly, to go too easily on some of its others) because it is a Woody Allen film, and if this were somehow the work of a new director, we'd all be warmly praising it as a promising debut. It could not, of course, be the work of a new director; for all of its faults, it is quintessentially and definitively an Allen film, more than anything he's done in a while.
But no, it is not "great Allen", even if it is otherwise a supremely characteristic work. At the same time, I cannot bring myself to call it "bad"; what it is, beyond doubt, is unsuccessful, though part of the reason it gets there is by being one of the strangest and, in its own way, most ambitious movies of the director's career. The one thing I refuse to do is file it away as the same kind of lazy "Woody needs a project" filler as Small Time Crooks or Cassandra's Dream; it is certainly not a lazy movie. It's a heady, conceptual movie, full of many odd and unusual ideas it wants to try out in telling its multiple stories. That Allen fails at executing nearly all of these ideas is a problem; that he is still interested in pushing and challenging himself this many years into his career is a comfort, though not an especially warm one.
(I am reminded of 2004's Melinda and Melinda, the last time Allen tried to play this much with form and structure; it too was a failure in almost every regard, and an equally noble one).
The film starts with a traffic policeman (Pierluigi Marchionne) pausing in his duties to stare right into the camera and tell us that thanks to his job, he gets to spend a great deal of time observing the comings and goings of people in Rome, and he finds their stories to be all just perfectly fascinating. Fans of anthology movies will recognise this as the cue for a cluster of completely unrelated stories united, vaguely, by theme: no mistake, either, that Allen's Italian film should be an anthology, as that form is predominately Italian, although any hope that this means the influence of any '50s or '60s Italian filmmakers will creep into the feature is quickly dashed: it looks and talks exactly like a Woody Allen picture, though the golden, dappled cinematography by Darius Khondji gives it a far more swoony, poetic look than the great bulk of the director's career (it is not so much About How Rome Looks as Midnight in Paris was about its own title city, but New York hasn't looked so invitingly cinematic in an Allen picture since the 1970s).
Breaking with anthology tradition, the four stories featured in To Rome with Love aren't separated out as individual short films, but cross-cut between one another; one of the film's many bold choices that doesn't work (all four stories would benefit from being segregated, not least because Allen would thus be obliged to be a bit more disciplined about his storytelling). These stories are, in no special order: a farce about a newly married couple in from the country, Antonio (Alessandro Tiberi) and Milly (Alessandra Mastronardi), who become separated by the confusing layout of the huge city, and the complications that arise when Antonio has to beg a prostitute, Anna (Penélope Cruz) to pose as his new bride in front of some family friends; a satire about a regular working man, Lepoldo (Roberto Benigni), who wakes up one day to find himself quite unaccountably one of the most famous men in Rome; a light charater comedy in which a young couple, Hayley (Allison Pill) and Michelangelo (Flavio Parenti), introduce their parents to one another, with her dad, Jerry (Allen himself), a former opera director, trying to cajole Michelangelo's dad Giancarlo (Fabio Armiliato) into sharing his awe-inspiring shower-singing voice with the world; and a disaster, in which Alec Baldwin...
Actually, let's dig into the Baldwin sequence a bit, because it is both the film's most experimental sequence and by far its worst. For starters, it's one of two segments in which we're set up to expect one person as our protagonist, only to see that quite without fanfare, they turn into just window dressing (Michelangelo is introduced as the "star" of a sequence primarily about Jerry). Baldwin's John, an architect revisiting Rome after 30 years away, pokes into the neighborhood where he lived for a year to find young American ex-pat Jack (Jesse Eisenberg), who is quite a lot like he was as a kid in Rome, living with his girlfriend Sally (Greta Gerwig). Sally's friend Monica (Ellen Page) is landing in Rome to get away from a bad breakup, and this is where things get to be phenomenally weird, because it turns out that Jack isn't just like a younger version of John, he is the younger version of John, and John keeps drifting in, offering advice - but not in a fantasy way, because when he does so, the film sort of "stops" and the three young people all can see him and interact with him, though the things they discuss do not thereafter inform their actions or knowledge. Basically, Baldwin is playing a non-diegetic character, criticising his young self for being such a dipshit but unable to change the mistakes of his youth simply by having more knowledge: it's a phenomenally intriguing concept that goes fucking nowhere, in part because Allen's filmmaking style at this point in his career is too spare and laid-back to handle that kind of inherently surreal notion (it's possible to imagine the same idea getting made right around Annie Hall, and proving just as much a structure-bending masterpiece as that movie is), and in part because the acting is a nightmare: plainly, Eisenberg, Page and Gerwig must have been over the moon at the chance to work with Allen, one of those directors who can get A-listers to take teeny-tiny roles just for the honor of having worked with him (as Baldwin himself does in this sequence); but at least two of them have no business trying to deliver his arch dialogue in their customary acting styles. Gerwig and her naturalism are buried alive in a character that needs the exact opposite of her retiring simplicity to register with the audience at all, while Page gives her career-worst performance as her customary snotty quirk jams against a particularly un-insightful Allen Woman and all that is worst about her acting and his writing are brought to the fore in a character that could not possibly be less believable or enjoyable to watch.
None of the other three are nearly so dreadful - in fact, the Antonio/Milly farce is generally quite funny, though it lazier than a writer of Allen's skills should feel comfortable with - and there are flashes of genius-level Allen throughout, though mostly at a theoretical level, such as the way that the four stories represent four different types of comedy that Allen has worked with in his career, but never all at once like this. To diminished results: the farce, as I said, is lazy rather than sparkling, and the satire, though blessed by an uncommonly reined-in Benigni performance, has very little original or intelligent to say about celebrity (though it is both more original and more intelligent than Celebrity). The segment with Jerry ends up being perhaps the most effectively smart, owing to having the strongest performance in the film (Judy Davis, wasted but brilliant in the small role of Jerry's wife and irritated conscience - her snappish "Your brain has three ids" is the best line delivery in an Allen film in a long time), and because Allen plays the film's most clear-cut "Woody Allen Character" himself, the presumptive retirement of Scoop being wiped away for no reason, except that it makes the fairly un-oblique discussion of Allen himself a bit more tolerable. "You view retirement as death", says Davis several dozen times in minor variations, and Allen-Jerry's wounded reaction is palpably autobiographical; his rejoinder to the many critics who, observing his limp batting average over the last 15 years, would maybe like him to slow down and try not realising an uninspired, quota-filling movie every year. It is the closest the director is ever likely to come to stating outright that if he slows down, he will stop completely; he's not making movies compulsively but fatalistically.
That's a dour undertone to a ditzy comedy, particularly once you realise that it's the key not just to Jerry, but to the entire film: for what is To Rome with Love if not an investigation into all the things Woody Allen has done with his career and his life, a mixture of several distinct but equally Allenish modes of comedy as performed by people at several different ages. There's a filmmaking-as-therapy tone to the film that, once noticed, doesn't go away; it certainly doesn't make it any more "effective", nor more entertaining, nor funnier; but it makes it tremendously interesting. Judgments of good or bad aside, it takes a brilliant filmmaker who long ago ran out of things to prove to make something that's this probing and self-reflective while also being this light and fluffy.