“A walk down 14th Street is more amazing than any work of art,” Allan Kaprow wrote in 1959, the same year he staged 18 Happenings in 6 Parts in a loft a block off the Bowery. What might he have said of that mile-long boulevard, “one of the great highways of humanity” per Theodor Roosevelt (the only New York police commissioner ever elected US president)?

The greatest architectural hodgepodge of its borough, the Bowery (from the Dutch bouwerie, meaning “homestead”) recapitulates the history of lower Manhattan. First a Lenape trail and then a sylvan lane, it was a briefly fashionable suburb before it morphed into New York City’s first working-class entertainment zone, a precursor to Times Square and Coney Island. In the late 19th century, the Devil’s Mile was an avatar of urban development—the site of an elevated train that cut a clamorous swath through the teeming neighborhoods of Lower Manhattan. By the early 20th century, the Bowery was the most famous skid row in America. A hundred years later it is the subject of a bold hybrid show at the New Museum.

“The Bowery: Devil’s Mile” opens with what might be a simulation of a show at the New York Historical Society—vintage maps and a 200-year-old marble milestone join 17th-century prints, among romantic views of no-longer-extant or never-existing Native villages. An imperious early 19th-century oil portrait of New Amsterdam’s irascible, much mythologized Director-General Peter Stuyvesant is upstaged by another, less decorous canvas from the same period by an unknown artist of the infamous Five Points slum, just a few blocks west of the Bowery. It’s a copy of George Catlin’s 1827 print, presenting a blurry Brueghelian tumult from a Caillebottesque perspective, that became something of an icon: Catlin’s image emblazoned the cover of Taylor Einbinder’s 2001 history Five Points and informed the design of Martin Scorsese’s 2002 passion project Gangs of New York.

Topical print images of newsworthy riots and fires give way to all manner of ephemera—tickets, handbills, souvenir postcards, stereo views, broadsides, and songbooks, not to mention advertisements for the dime museums and variety theaters that lined the Bowery from Chatham Square to Cooper Square throughout the 19th century. While much of the earlier material is culled from the New York Public Library, the most sensational paper artifacts mainly come from the collection of local archivist Adam Woodward, who has also provided the gallery’s centerpiece: a resplendent enameled 1836 pump wagon that once belonged to the volunteer firefighters known as the Lady Washington Engine Company No. 40.

The pump wagon’s relevance to Bowery culture will only be apparent in the exhibition’s final gallery, which is dominated by a comparable artifact, Brad Kalhammer’s installation Bowery Nation (1985–2012). A mélange the actual Devil’s Mile may be, but its representation is disinclined to break with historical chronology. This becomes clear when, moving on from ephemera, the exhibit turns cerebral. A ten-minute slideshow of the Danish journalist Jacob Riis’s photographs of hovel-housed immigrant families, accompanied by excerpts from his 1891 book How the Other Half Lives, is juxtaposed with Martha Rosler’s cool photo-installation, The Bowery in two inadequate descriptive systems, made some eight decades later. Whereas Riis uses documentation to expose, Rosler questions conventional representation. There are no people in her piece, simply 45 silver images of Bowery storefronts and gutters, typically littered with empty bottles. In lieu of captions, these are paired with placards giving slang terms for alcoholic intoxication. Nevertheless, Riis’s reportage washes over Rosler’s grid.

One feels the absence of Lionel Rogosin’s 1956 hybrid documentary On the Bowery. Instead, the show’s lone motion picture is a loop of the 1902 Edwin S. Porter comedy, How They Do Things on the Bowery, in which a visiting rube is lured into a Bowery saloon to be drugged and robbed. But the show more than makes do with the photography that comes to the fore in a long gallery featuring WPA work by Berenice Abbott and the photojournalist Weegee, as well as the younger street photographer Harvey Wang. There’s also a spooky Reginald Marsh canvas The Bowery Strokey’s Bar, painted in 1953 (the year before the artist died), in which a tabloid lies on the spectral pavement with the headline “Atom Bomb Burns Out Ghost Town.”

Taken by David Gadis, late 1970s photographs of the landmark punk venue CBGB (but not curiously an example of the club’s aggressive DIY handbills) segue into a small room devoted to Nan Goldin’s The Ballad of Sexual Dependency (1979-96), heralded as a barker might by its curated soundtrack. The outstanding artwork of the exhibition, Goldin’s slideshow, largely devoted to candid portraits of friends, many shot in her Bowery loft, remains stunningly raw. The emotion-charged images are simultaneously immediate and elegiac.

Exiting The Ballad, the viewer comes face to face with a white wall of 28 portraits in a variety of mediums by a fellow diarist and Bowery artist Billy Sullivan: The juxtaposition of these two vibrant portrait galleries is one of the show’s big ideas. The wall is flanked by works by Lynda Benglis, Eva Hesse and Tom Wesselmann, presumably produced in their Bowery lofts. (Context makes them newer iterations of the 1822 milestone.) The centerpiece is Kalhammer’s assemblage of 22 spidery birds and perhaps a hundred kachina dolls fashioned from found objects and refuse mounted on a sawhorse-supported twenty-five-foot-long wooden plank. Kalhammer’s Bowery Nation, which could have given its name to the exhibition, conveys the show’s intensely personal civic pride—its Campanilismo. Broadway is for tourists and celebrities, but every New Yorker has a Bowery connection. As for me, I can brag that, before World War I, my Polish-born grandmother was a 19-year-old barmaid at a dive near East 2nd Street, site of the Tin Palace jazz club, now an upscale pasta joint closed for renovation.

“Devil’s Mile” is a relatively compact exhibition but, in the tradition of the Bowery’s bare-knuckled boxing saloons, it punches above its weight. The show’s audacious yet unstated premise is that, as assertive a presence as anything else on the street, the physical New Museum is of a piece with the concert halls, curiosity cabinets, menageries, sideshows, beer gardens, Yiddish theaters, and Christian missions, not to mention nickelodeons, tattoo parlors, pawnshops, barber colleges, flop houses, wholesale lighting joints, and jazz clubs that have lined Roosevelt’s highway of humanity from Cooper Union to Chinatown. That it is, in other words, not only new, but a continuum.