With "To Rome with Love" Woody Allen may have achieved his best integration of humor and insight. He follows four stories: an Italian-American romance (Allen plays the father of an American tourist who takes up with a Roman lawyer), a couple from the countryside, an ordinary middle class Roman who becomes suddenly famous for no reason and a famous architect who has the opportunity to look in on, and advise, his younger self. The overall theme of these stories (which do not, in fact, intersect) is the question of what one wants out of life, the value of one's contribution and whether fame matters. Allen's character, like Allen himself, feels desperate to make his mark, even in retirement. The entire question of one's lasting contribution is considered by an architect who dreamed of greatness but made a name for himself designing shopping malls, who refers to "Ozymandian melancholy."
I met a traveller from an antique land
Who said: Two vast and trunkless legs of stone
Stand in the desart. Near them, on the sand,
Half sunk, a shattered visage lies, whose frown,
And wrinkled lip, and sneer of cold command,
Tell that its sculptor well those passions read
Which yet survive, stamped on these lifeless things,
The hand that mocked them and the heart that fed:
And on the pedestal these words appear:
"My name is Ozymandias, king of kings:
Look on my works, ye Mighty, and despair!"
Nothing beside remains. Round the decay
Of that colossal wreck, boundless and bare
The lone and level sands stretch far away.
- Percy Bysshe Shelley
Another theme is marriage and infidelity. Our young architect struggles with whether he should sleep with his girlfriend's best friend (against the advice of his older self, who tags along, like Jiminy Cricket, to offer advice). As a newly wed bride from the countryside decides whether to sleep with a movie star, she considers that she would regret not being able to tell her grandchildren that she had! A chauffeur offers the view that the wives of famous men understand they must share them with the public, and (later) that, overall, it is better to be famous. It is impossible to watch this movie and not think of Allen's personal life, which is widely considered scandalous, although he himself said recently in the Washington Post that views himself as "very average, middle class. I get up in the morning, I have a wife and kids, I work, I’ve been productive, I practice my horn, I go to ballgames, it’s a normal kind of thing. I have some quirks, but everybody has some quirks."
Those quirks present yet another theme. Despite fame (or not), despite romance with the beautiful people, the characters are who they are. Our famous nobody is asked his preferences for breakfast food, and whether he wears boxers or briefs. The young Roman lawyer's father sings opera brilliantly, but only in the shower, when he is naked. I think this theme underlies the decision to open and close the film with "el blu dipinto di blu" (Volare). It is the unsophisticated choice of an American tourist of a certain age, which, after all, describes Woody Allen. Ultimately the characters all return home, to their spouses, their family, their homes.