One of the classic ways not to embrace failure is to hide it away.

City Island is a colourful parable of ‘just your average family’ where every one is sequestering some dark secret. As Molly says, “It’s a ruse you see. Because Vince has feelings of shame and inferiority about his ambition.”

The thing is that that the secrets aren’t quite a dark as they first appear. The director creates a character arc where more importantly than the character changing is the audience’s perception of them changing as the context of their ‘failures’ gradually get exposed. A perversion that actually reflects a giving spirit. A sordid job that actually reflects a personal accountability. A lust that actually reflects a long stifled romance. A furtive ruse that hides a creative ambition.

The foil and catalyst to all this personal discovery is Tony. While the rest of the family is playing the parts of middle-class Americana, Tony portrays an overtly abject failure. A lifetime criminal son of a ‘whore’. But despite his true and graver failings, he is completely open and honest about himself. In the climactic reveal he rails against Vince laying bare the idiocy of their running from their failures…

“Fine, do it [send me back to prison]…at least everyone there is honest. You’re so scared of your wife, you won’t even smoke in front of her. And you got your wife thinking you got a girlfriend because you’re too scared to tell her you want to take an acting class.”


The ultimate lesson is that hiding the failures cause more harm than the failures themselves. In fact, when the failures are finally embraced, bonus dividends accrue. The most prominent is in the rekindling of Vince and Joyce’s romance. As Molly portends,


“The Vincent she never knew is the Vincent that she secretly wants back.”