"New York, New York" -- in case you missed the subject of the show, they named it twice -- is a massive exhibition of approximately 500 works by 200 artists organized by Guggenheim director Lisa Dennison and adjunct curator Germano Celant for the 4,000-square-meter Espace Ravel in Monaco's six-year-old Grimaldi Forum cultural center. With a price tag in excess of $2 million, the show is an admirable effort to add some high culture to Monaco's typical mix of gambling and visits to the royal palace. Last year's effort focused on the arts of Africa [see "Monaco, Africa," Aug. 12, 2005], and in the works for 2007 is a show devoted to Princess Grace.

A meandering tour through a half century of art made in and about NYC from the 1950s to the present, "New York, New York" stakes claim to an awful lot more than Manhattan Island, everything in the world that is cosmopolitan and urban and full of juice, in fact. And as New York has the world, so the world has New York -- such is the message of a black-and-white picture Lee Friedlander took only a few years ago, a photo of Las Vegas (2002) that nevertheless features the Statue of Liberty and some kind of Manhattan skyline. Not for nothing is New York the home of take-out. Call it "New York to go."

An ambitious exhibition like "New York, New York" deserves an ambitious exhibition design, and Italian designer Pierluigi Cerri has provided one. He has structured the show's layout according to a street grid. At its center is an acute angle meant to evoke the Flatiron Building. Darkly carpeted "avenues" run more or less in one direction, with "streets" branching off of them. High gray walls evoke a cavernous Manhattan scale and density. Cerri stopped short only at dressing the security guards in NYPD uniforms.

The corridor walls are, of course, lined with art, as are the white-walled galleries within. Photographs are interspersed with paintings, and sometimes arranged in a horizontal band, an effect that resembles a news ticker. It's the maze of New York, the straightforward street grid in which you can easily get lost. Performances are presented on video monitors, and film clips in small theaters with benches, divided by category (film noir, musical comedies, experimental).

Artworks on view range from Arshile Gorky's 1945 Landscape-Table (on loan from the Centre Pompidou), to a recently completed work by Tom Friedman testifying to the ridiculous fragility of life. In between is a long march through a huge number of works by the usual suspects -- they do add up, don't they? -- Jackson Pollock, Willem de Kooning, David Smith, Robert Motherwell, Frank Stella, Andy Warhol, Carl Andre, Jean-Michel Basquiat, Kiki Smith, Cindy Sherman, Laurie Simmons, Nan Goldin, Keith Haring, Jeff Koons, John Currin, etc. It's everything the curators think you need to know about 50 years of art, from Acconci to Wojnarowicz.

Familiar though the show may be in concept, it still contains surprises that make a visit worthwhile. Richard Pousette-Dart's 1971 Hieroglyph (White Garden) is a serene vision of infinity, a grey-green sea of nuances that is welcome, though it hardly seems very metropolitan. More overtly American are the two works by Tom Wesselman, Still Life #45 (1962), literally a turkey in a frame, and Bedroom Painting #36, complete with a bunch of flowers and an open-mouthed woman, either dead, asleep or awaiting someone special.

One jewel is Ad Reinhardt's 1956 Abstract Painting with its wonderfully differentiated shades of black, along with a nice comparison painting from 1952 in which Reinhardt located rectangular bolts of color systematically against a pinkish background (a composition that today seems positioned somewhere between Mondrian and Matisse and a computer-generated image). Missing, in a Reinhardtian context, are some of his satirical drawings mocking the 1950s art world and its many pretensions.

Also missing, while we're on the subject, are works by Marcel Duchamp, who adopted New York as his home just as much as de Kooning and Robert Frank did, as well as works by the late, great Leon Golub (1922-2004), whose spirit still looms large over the downtown New York art scene. Of course, you can't have everything.

One notable installation was a set of massive, balloon-like shapes with interior projections by the international architecture and design team known as United Architects. In Projection of a Film on Inflatable Structures, images of the street and the city come at viewers centrifugally on "screens" that resemble zeppelins. Architecture in exhibitions is typically limited to models, sketches and photographs; here, the audiovisual construction gives a sense of real volume and space, a melding of sculpture and sound that imitates the claustrophobia and cacophony of the street.

While the art invokes a rarefied esthetic realm, the photography repeatedly pulls the viewer back down to street level. William Klein's group portraits of 1950s Harlem, for instance, are apt reminders of the culture of street-level performance that is everywhere in the city. Diane Arbus and Helen Levitt give viewers more of the same, and of course WeeGee's corpses and police arrests are anything but uplifting -- down to earth, in fact, far down. Eventually the two strands of artistic practice make a point of merging, notably in the works of Andy Warhol, with his electric chairs and Hollywood celebrities (there we go again, wandering out of the real city) and all of his many followers.

One thing becomes clear -- "New York, New York," like New York City itself, can seem to be all about winners: artists like Frank Stella, seen with his geometric and "baroque" phases juxtaposed, and '80s figures like Julian Schnabel and David Salle and the inescapable Koons. The show is a proud boast on behalf of New York, not an archeological enterprise.

Among the more contemporary works is Kara Walker Campton Town Ladies (1998), the artist's trademark silhouettes of rebellious black children from the antebellum South, which ends with an image of a pile of shit that is labeled, in case we needed telling, "The End." It's just a tease, since the show doesn't end there, although Walker's pessimism does hit a somber note.

Probably my favorite works in "New York, New York" are the two sculptures by the puckish Friedman. The deceptively simple White Cloud (1989) is four lengths of taut string stretched from floor to ceiling, making an invisible rectangular column around which the artist has carefully wound a spiral of toilet paper, tightly at the top and then loosening and slipping off at the bottom. Sheer is an understatement for this work, which invokes infinity with a material even more base than sand. And five years after 9/11, White Cloud is an unmistakable reference to the World Trade Center, the prototype of mistaken permanence from a still-ominous time.

Friedman's materials are even more base in Inside-Out, a construction assembled between 1991 and 2006. Out from an inverted cardboard box extends a peninsula of stunningly delicate trash and ephemera that seems laced together like a 3D collage. Friedman's gentle kind of fleurs-du-mal construction has rather more grace than the brazen assemblages of the Swiss political artist Thomas Hirschhorn. Everything feels fragile here. You come away wondering whether life is not useless but priceless, or the other way around.

Monaco is a short drive from the Matisse Chapel in Vence and the beguiling Fondation Maeght nearby. The Matisse Museum in Nice and the Renoir House in Cagnes are also in the area. Admission to "New York, New York" is €10 euros, and parking is a mere €3 euros more -- certainly less than the cost in the real New York, N.Y. You can gamble away the rest a short walk away.

DAVID D'ARCY is a correspondent for the Art Newspaper, a contributing editor at Art & Auction and a regular critic on the "Front Row" program on BBC Radio.