‘How many roads must a man walk down / before you call him a man?’ Is Bob Dylan’s most famous protest song really a surrealist riddle? What’s the road made out of, and will it hurt the tender soles of my feet? That’s the thing about the Jewish experience, particularly when it comes to the arts, it’s open to debate and metamorphosis – Prague’s most famous Jew, Franz Kafka, will tell you all about that.

Indeed, a certain kind of reflection and self examination can be traced back to the silent ghetto melodramas of pre-World War One Europe and the ‘almonds and raisons’ crowd Yiddish cinema craze that later spread west to influence American moviemaking indubitably, undoubtedly and forever. These films, which had names like Blood of the Poor, Solomon’s Son and Love in the Ghetto, focused on specific problems of the immigrant experience and often ended in a moral ambiguity (evil deeds by corrupt landlords generally went unpunished) that was totally out of step with their time.

Two wars, the Holocaust and the viral-like spread of psychiatric and critical theories courtesy of some of Europe’s more comfortable Jews, Marx and Freud (plus one retreating Protestant – Carl Jung), cemented the Jewish experience (with all its inherent tragedies and humour) as central to that of American cinema. Mel Brooks, Zero Mostel, Elliott Gould, Woody Allen, George Segal, Carl Reiner among many other brilliant artists became the celebrity face of ‘God’s chosen people’. For a while self doubt, urbanity and an obsession with forbidden fruits were all that mattered in long neglected hippy era comedies such as Where’s Poppa?, Portnoy’s Complaint, Move, Minnie and Moskowitz, Little Murders, and of course Allen’s Play it Again, Sam.

The kind of progression and debate that these wonderful films offered died with the revival of a certain type of WASPy 80s action hero, but Charlie Kaufman’s remarkable absurdist fantasy Synecdoche, New York (pictured) offers at least a partial return to these giddy celebrations of self analysis and surrealist humour. Detailing the later life of gifted theatre director, Caden Cotard (Philip Seymour Hoffman), as he attempts to create a work of brutal realism and honesty by restaging his own troubled, hypochondria-plagued life with an ensemble cast in a large warehouse in Manhattan’s theatre district, Synecdoche, New York is an ingenious, ambitious conundrum that’s underlined by themes of symbiosis, connectivity, deterioration and an understanding of our dream life selves that is both beautiful and horrific.

Kaufman’s previous nutty and inventive work as screenwriter – Being John Malkovich, Adaptation, and Eternal Sunshine of the Spotless Mind – has proved that he is no stranger to conceptual semantics and modish ennui, but Synecdoche, New York is something else. It’s a work of depth and scope to rival the daddy of all identity crisis dissertations, Fellini’s 81/2. It’s the riddle inside the enigma inside the pessimist’s Kippah. How many roads must a man walk down? Too many and not enough.

Synecdoche, New York is on selected release from Fri 15 May.