We have all heard John Kander and Fred Ebb’s title song about a million times, usually crooned by that old smoothie Frank Sinatra. “I want to wake up, in the city that never sleeps…” You know the rest. It’s a song that has become an anthem for the city for which it was named. It is now legendary.

What you probably didn’t know was that this song wasn’t penned by or for Old Blue Eyes, by any stretch of the imagination. It was written by the world-famous songwriting team for Martin Scorsese’s 1977 extravaganza New York, New York—a throwback/homage to the big studio confections of the ‘40s and ‘50s, many of which were directed by star Liza Minnelli’s father Vincente, and starring her mother Judy Garland.

So it makes perfect sense that the song was commissioned by a director and star (Robert De Niro) who has so closely been associated with the Big Apple, and an actress whose very genes were permeated by the genre, and who would also become known most for her Oscar-winning, tune-belting role as Sally Bowles in Cabaret.

In retrospect, and on paper, these pedigrees seem to be a match made in heaven. The finished product, though, is a little bit messy, a little too glossy, and a lot too long (almost three hours!). Candy-coated, and unnaturally colorful, the film opens on VJ Day, 1943, on the streets of New York City. Minnelli’s Francine Evans and De Niro’s Jimmy Doyle meet cute in a USO hall and from there, what passes for a plot unfolds as the firecracker romance between the two becomes the catalyst for the lumbering story.

New York, New York, under a haze of manic glitziness, is ultimately a story about two creative people, on their way to fame, who find it impossible to coexist with or without each other. It is an old-school premise that the director lifts directly from the films he watched as a boy. There’s even an extended scene (which the director says on the extras disc was intentional) that mimics Garland’s “Born in a Trunk” number from A Star is Born (to which Scorsese’s film basically owes everything) but flops.

What Scorsese tries to do, in an era where the musical was mainly dead, is reinvent the genre by mixing the gritty realism of the lives of musical performers on the road, trying to survive in post-World War II New York City with the Busby Berkley-esque flights of fantasy clumsily interspersed with hearty doses of tough Scorsese reality. He celebrates the artifice of the form with obviously painted sets, sparkly costumes, and other whimsical touches throughout.

It’s virtuosic, and ambitious, but feels hollow and ill-conceived, relying too much on improvisation between the actors – De Niro and Minnelli are a downright bizarre match. Sometimes they have chemistry, other times, they’re flatter than pancakes. Minnelli looks blatantly uncomfortable improvising opposite consummate Method man De Niro, though in her interview on the extras disc, she recalls the making of the film with clear affection.

The director’s eye for casting, however, is impeccable. This is a man who has led Don Rickles and Jerry Lewis to their career-best performances. Casting Minnelli was maybe the smartest move on Scorsese’s part. No director (other than Cabaret’s Bob Fosse) has ever elicited such a humane performance from the hard-to-cast Liza.

Scorsese films her like a ‘40s musical screen goddess, and she repays him with one of her most relaxed, assured acting performances. Scorsese if often accused of being a macho director of men, but it should be pointed out that he has guided 13 women to Oscar nominations. Even though Minnelli was not among the nominated women, it is clear that she took the opportunity and ran with it.

Curiously, the hyphenate’s dramatic scenes are the ones to watch – her attempts at establishing and nurturing her character are valiant and more interesting than her by-the-numbers musical sequences. In fact, in the scenes that should have been a lot more bombastic, the main thing you notice is how awful Minnelli’s lip-synching is.

De Niro, after Taxi Driver, should be commended for stepping as far away from Travis Bickle as he possibly could. The actor is very much outside of his comfort zone as Jimmy, but the stiffness sometimes shows through.

If this film feels dated, that’s on purpose, according to the director. The real mystery, though, is how does this fit overall into the director’s oeuvre? It functions as another New York story, which the director has become synonymous with, it is another “Marty/Bobby” collaboration (their third out of many), and it is another film that romanticizes the director’s adoration for the medium and the moving images that shaped him as a child – likely the most prevalent theme in all of his work.

Scorsese’s insistence on old-school craftsmanship, his slavish devotion to the classic forms of the musical, make the film’s flop even more devastating. It is clear he went into this project with high hopes. Even now, there is a sense in watching him talk about the film, that he is still disappointed by the reception.

The seeming innocuousness of New York, New York belies its actual construction. Yes, this is a clear genre picture, but one that was made immediately following the relentless, ground-breaking Taxi Driver—one can only wonder which film proved more of a challenge for the director to make.

Still, it is hard to really see this as more than an exercise in nostalgia. The director’s customary passion is there, but there is still something that feels uneven. The Scorsese stamp, however, still holds more credibility and style than a dozen Dreamgirls or Hairsprays. But, unfortunately, this is more of a study in cinematic excess and directorial indulgence. New York, New York is a well-intentioned, well-built oddity. It is reminiscent of other big, noble musical failures such as Woody Allen’s wooden Everyone Says I Love You and Robert Altman’s Popeye.

The failure of New York, New York, after the critical success of Taxi Driver (1976), allegedly sent Scorsese into a tailspin of depression and addiction. In the introduction on this special edition, Scorsese reflects on the picture being “unmanageable” and calls the style “un-definable”. His eloquence and willingness to defend what is likely his worst film, combined with a fearless sense of experimentation, should put to rest any doubts that Scorsese isn’t one of the most consistently interesting American filmmakers.

After seeing this, I couldn’t help but wondering what the modern, mythic filmmaker Scorsese, who has so lovingly embraced new movie-making technologies and aesthetics would do with a musical today. The results would likely be much more vivid and alive.