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  • Writer's pictureKristy Calabro

(S)OLD NY: A lesson in Art, History, and NYC

Old NY is dead. You hear that a lot from New Yorkers, those who stayed and those who fled. It may be different, but it's never dead. Anything can change in a “New York Minute.” Old NY never goes away. It’s always with us. We are our past. A culmination of everything and everyone that has come before us.

When you walk down a NYC street, imagine who may have preceded you. You’re perhaps taking the same path as Emma Goldman on her way to an anarchist meeting on Suffolk Street, following the footsteps of Nikola Tesla visiting Thomas Edison on Houston Street, or taking the same route as William S. Burroughs heading home to his "Bunker," at 222 Bowery. You can still feel echoes of Keith Haring making chalk drawings over by the Jay Maisel/Supreme building near Spring Street, Basquiat on Great Jones, or David Bowie on Lafayette. Some artists have such an impact that their very souls are embedded into the DNA of this great city.

Creative, radical minds inspired and made NYC what is it today, and the city inspired them. Another reciprocal relationship is public art and graffiti influencing the streets as much as the streets influence the art. Do you ever wonder how certain sites become definitive places where fans and photographers discover the latest art pieces? Sometimes all it takes is for an artist to make a risky, split-second decision to put up their work and others will follow in their trail. Leaving one mark can turn a location into a landmark.

In this series, we’ll explore some of these locations and learn about art, history, old and New York. The past is key and it unlocks the door to the future. So, where should we start? Let’s take a street art stroll down "The Alley."


Photo by @kristycnyc


There are at least 20 alleys in lower Manhattan alone, but if you are a fan of street art and graffiti and someone says, "meet me in the alley,” you probably know where to go. On the north side of Rivington Street between Bowery and Chrystie Street is Freeman Alley. One of the most famous graffiti spots in NYC, it's become a hub of public self-expression. It’s well-known now, but for a long time, Freeman Alley didn’t even have a street sign and was taken off of city maps in the 1900s, like it didn’t even exist.

Where did it go? Who is it named after? What was it used for? Why would anyone decide to commit vandalism down a one-way alley? So many unanswered questions that we hope to uncover by the time we reach the end of the alley, which happens to be the very popular Freemans Restaurant.

Photo by @kristycnyc


1868 Map, (NYPL)

Freeman Alley, Wagon House and Stables.Christie aka Chrystie Street, Rivington (left)

Bowery (top) where in the 1800s, you would find variety theaters and saloons


In the book “The Lower East Side Remembered and Revisted,” by Joyce Mendelsohn, it says, Freeman Alley was originally a country lane, and the name is still disputed today. Some believe it is named after Uzal W. Freeman, a 19th-century city surveyor who lived on the Bowery and others think it refers to the road leading up to the second African American burial ground, now the site of the Sara D. Roosevelt Park near Chrystie, between Stanton and Rivington. One last theory is that the alley refers to a former slave, Anthony (Antony) Congo. A newly "freedman" of New Amsterdam, Anthony was granted 6 acres of land that today includes, the New Museum and Freeman Alley. This became the first free Black settlement in Manhattan.

The Bowery Mission moved to its current location in 1909 and directly behind it is Freeman Alley where hungry men would form bread lines every night. Around 1914 the alley was demapped and the city removed any responsibility or upkeep associated with it. A few decades later, in the 1960s artists started coming into the neighborhood and moving into lofts. 222 Bowery was a former YMCA that became completely occupied by artists like Mark Rothko and William S. Burroughs. 6 Rivington Street was formerly a Salvation Army women's shelter that also turned into lofts, where artists like Bob Thompson moved in and had a studio. This area is rich with art history.

Freeman Alley Archival Photo and Freeman Alley, Present Day (2021) photo by @kristycnyc


There are a few turning points in the evolution of graffiti and street art in NYC. First, 1981 was a pivotal year. The Fun Gallery located in the East Village was launched by Patti Astor and Bill Stelling. This is important because it brought graffiti into the NY art world. Artists like Haring, Basquiat, Futura, and more showed at Fun Gallery. Second, the same year saw Jean-Michel transition from the streets to the studio. Basquiat, "the genius of the streets," after showing at Fun, showed with Annina Nosei in Soho. Lastly, when Keith Haring opened the Pop Shop, he commodified street art, where you can take an image once seen on a subway wall, make it portable, and put it on merchandise. Historical NYC moments like these helped legitimize street art and graffiti, brought them into the world of fine art because they were highly marketable and profitable art forms.

"I know Bill Stelling and Patti Astor, (owners of the Fun Gallery) that brought graffiti into the art world...the first time graffiti artists had a foothold into the NY art world." - Jimmy Wright

#1 Freeman Alley is a former horse stable turned marble factory turned residence, owned by the artist, Jimmy Wright. If you visit the alley often enough, you’ve probably had the good fortune of bumping into Mr. Wright who has lived here since 1980. He's a wealth of knowledge and always greets you with a warm welcome. The alley may be a fun spot to see art or a place to have your next brunch date, but for Jimmy, it's home. #1 Freeman Alley is 3 floors of artist's lofts and the first tenant of Jimmy's on the ground level was a Chocolate Factory, today it's the art gallery Salon 94 Freemans.

Since it was removed from maps, there wasn't a "#1 Freeman Alley" yet; the building was originally known as "8-10 Rivington Street rear." Jimmy applied for an address change and the Manhattan Borough President’s office granted him #1 Freeman Alley. It's all thanks to Jimmy that Freeman Alley has a street sign. He paid for the sign and paid for the city to put it up. Before this, he hand-painted street signs on the side of 8 Rivington for the alley otherwise he would have never received any mail or deliveries. The Freeman Alley street sign officially went up in 2000. Jimmy also got street lights installed and in 1980 there were no scheduled garbage pick-ups and so his partner became a member of the community board and worked with the sanitation committee to reinstated them. Jimmy Wright knows that if you have to get something done, you have to do it yourself, like a true New Yorker!

The alley and the surrounding streets looked very different 40 years ago. In 1980s, Rivington Street was the worst drug block in all of Manhattan, it was where you went to get your heroin fix. A Dominican gang ran the street, but the territory was controlled by John Gotti and the Gambino crime family, who most likely received a cut of their drug sales. This sounds like the plot of a Martin Scorsese film. However, it's not fiction at all, but the reality of living on the LES of Manhattan in the 70s and 80s. The burned-out remains of a stolen car, homeless, addicts, gangs, the mob, muggings, streetwalkers; Jimmy has seen it all.


Mural by Cityarts Workshop (1970s)

This is when we start to see "Street Art" around Rivington Street. Plus Closeup of Freeman Alley

(*The building at the corner of Chrystie and Rivington was previously an empty lot.)

Courtesy of Artist, Jimmy Wright


Jimmy Wright was recently in a show at the Whitney Museum, "Around Day's End: Downtown New York, 1970-1986. He also shows with Fierman Gallery at 127 Henry St., has worked with DC Moore Gallery and Chicago's Corbett vs. Dempsey (named after the famous boxers.) He is best known for his series of drawings of the gay scene in NY from the early to late '70s. Jimmy was very active in the battle against AIDS. In 1991, his partner, Ken Nuzzo passed away from the virus and while Jimmy was his caretaker, he started creating giant, flower oil paintings in homage to his partner.

Photo of Jiimmy Wright by Joseph Dolton

Artwork by Jimmy Wright, Flames, Pastel, 41x29 in.


Seeing the alley through the eyes of Freeman resident, Jimmy Wright

Photo 1 & 2: Freeman Alley (1982) Photo 3: Silo Gallery (2004), Photo 4: Graffiti from (2007), Photo 5: Front of the alley starting to see wheatpastes (2013), Photo 6: Art vs. Ads turf war (2016-2017), Photo 7: Bride and Groom and El Sol paste-ups (2018)

Photos courtesy of Jimmy Wright


In early 2000s, the alley started to see graffiti tags, then a transformation of tags plus paste-ups. Stencil work followed and the latest evolution is paste-ups with a message. Jimmy likes it all and has noticed a demographic change where there's a lot more female artists doing paste-ups. In the last 6 months, Jimmy said, there have been very aggressive, huge graffiti tags going over the pastes, claiming more and more real estate on the walls in the never-ending battle between graffiti artists and street artists. But everyone can agree on one thing, we don’t like it when we see clean-up crews. Just last week, on Rivington Street, some spots were repainted and the art was covered up. Once a year, the Super puts a fresh coat of gray paint on the alley's wall. When this happens, you’re giving artists a fresh canvas to work with. There’s always going to be someone who has a need to express themselves, the “clean up” never lasts long.

How did it go from demapped to becoming a very popular destination? Freemans Restaurant changed everything. The day the restaurant did their first test runs, Jimmy said, was the day the homeless and hookers left Freeman Alley. Once the restaurant opened, it became the beginning of "safe passage" in Freeman Alley. The location at the very end of the alley gives it a feel of an exclusive hideaway that has attracted celebrities and hip crowds.

Freemans Restaurant (Established 2004.) photo by @kristycnyc


Photo from @freemanrestaurant Instagram, that's me @kristyncyc. Doing what else? Checking out some art


Being resilient, smart, resourceful; that's Jimmy Wright’s story, but it also defines the very nature of this great city. Every day is another opportunity to write a new chapter. The authors come from all walks of life. Students, scientists, poets, singers, and artists. Public art is a huge part of the identity of the city. Just like the rapidly changing Freeman Alley, New York City is ever-evolving as well. Like the artists who leave their mark in “The Alley,” the city leaves its mark on all of us. NYC, a timeless story that never gets old.


For more information:

Artist, Jimmy Wright

Instagram: @jimboalley


Freemans Restaurant

Instagram: @freemanrestaurant


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