The Manhattan Dentist Turning His Supermodel Clients Into Wanted Posters

A periodontist to roughly two dozen modeling agencies has spent a decade wheat pasting mugshots of the faces he treats, and a one-of-a-kind canvas from that run just surfaced on Artsy.

Dr. Nicholas Toscano spends his mornings inside a periodontal chair on East 63rd Street, examining the gums of some of the most photographed faces in fashion. He spends some of his nights wheat pasting mugshots of those same faces onto the walls of SoHo.

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Toscano is a board certified periodontist who has run Manhattan Periodontist since taking over the practice from Dr. Howard Wasserman in 2011, following a 13-year run in the United States Navy that included a General Practice Residency at Walter Reed National Military Medical Center in Bethesda, Maryland, according to a 2011 profile in Crain’s New York Business. That piece, written years before 1PENEMY existed, also describe him treating political fig during his Navy years and building his civilian practice largely through word of mouth and social media.

Word of mouth eventual carry him into fashion. Toscano is listed as the official dentist for roughly two dozen modeling and talent agencies across New York and Los Angeles, a roster that various profiles put at including Wilhelmina, IMG, One Model Management, Marilyn, Storm, Major Models, and Fusion. His patient list, per his own bio and several lifestyle write-ups, has included Victoria’s Secret names like Candice Swanepoel, Helena Christensen, Jasmine Tookes, and Josephine Skriver, alongside high fashion regulars like Andreja Pejic and Vittoria Ceretti.

It was through those patients, several of them working artists themselves, that Toscano says he found his way into street art. He has named fellow artists including Bradley Theodore, Tripp Derrick Barnes, and the muralist known as BY Flore among the roughly 100 artists he treats across New York, Miami, and Los Angeles, crediting time spent around their studios and shows for pulling him toward his own practice. Under the name 1PENEMY, shorthand for “number 1 public enemy,” a nod to the fact that unpermitted street art carries real legal risk, he began making work in April 2016. In a 2020 interview with Art Insider, he named Andy Warhol, Jean-Michel Basquiat, and Keith Haring as his biggest influences, a lineage that shows up quickly once you know what to look for: flat, repeated, instantly recognizable portraits of famous faces, built as much for a back alley as a gallery wall. His 13 years in the Navy, the same stretch that produced his dental training, also earned him two Navy and Marine Corps Commendation Medals and three Navy and Marine Corps Achievement Medals, credentials that sit oddly, and deliberately, alongside a body of work made under a pseudonym that translates to “public enemy.”

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Toscano’s first pieces, made that same year, were black and white wheatpaste portraits of four supermodels he had grown up admiring: Kate Moss, Stephanie Seymour, Brooke Shields, and Cindy Crawford. He rendered each in the visual language of a police mugshot, booking-style framing and all, then pasted them around SoHo, the Lower East Side, Meatpacking, Tribeca, and Brooklyn, treating four of the most photographed women of the 1990s as though they were wanted.

He has described the intent as a comment on the fashion industry’s habit of holding women to an impossible standard of beauty while, in his frame, treating them as products rather than people. In a conversation with Naluda Magazine, he drew a direct line to Warhol’s celebrity silkscreens of Marilyn Monroe and Liz Taylor, work that similarly flattened famous women into repeatable, mass-produced icons. Some later variations push that discomfort further, reworking subjects in the makeup of the Joker, a choice Toscano has said is meant to underline the expectation that women in fashion not only meet an impossible standard but perform good humor about it.

The composite image, all four mugshots arranged together in a row like a police lineup, became known as the Soho Model Lineup. A related, ongoing strand of the series that pairs models with their own street portraits goes by the name Model Mayhem. According to multiple profiles of the artist, Cindy Crawford reposted the piece to her own Instagram not long after it appeared on the street, a moment several of those same profiles credit as the tipping point that turned a neighborhood curiosity into a body of work collectors wanted to own. Models began stopping to photograph themselves in front of the installations, tagging his account, and by late 2020 Toscano was describing more than 30 active commissions and interest from several galleries. When he staged his first proper gallery show that year, held under New York’s tightest pandemic restrictions, he has said roughly 500 people came through and 75 percent of the work on the walls sold, an unusually strong result for an artist’s public debut in a city with almost no other art events running at the time.

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Paper and wall paste do not last, and Toscano’s mugshots have since been reworked, repeatedly, into mixed media on canvas. Gallery 23 NY represents a run of his 2020 canvases and lists them through its partner page on Artsy. The gallery itself is not a conventional commercial space: it describes itself as a nonprofit based in the Meatpacking District built around empowering underrepresented communities, and its main program, WeArtNY, runs hands-on arts education and career-focused classes for children, teens, and young adults, funded in part through donations and sales from its represented artists, 1PENEMY included. Individual 30 x 40 inch portraits from his 2020 output, single-subject mugshots of Kate Moss, Cindy Crawford, Kendall Jenner, and Karl Lagerfeld among them, are listed by the gallery at $16,500 apiece.

The Soho Model Lineup itself is a different object: a 40 x 40 inch mixed media collage on canvas, also dated 2020, sold as a unique work rather than part of an edition. That sets it apart from a later, smaller version of the same composition, a signed 26 x 40 inch print in an edition of 25 that Gallery 23 NY sells for $350, meaning the piece now listed on Artsy is the one-of-a-kind original that started the series rather than one of the more widely distributed reproductions that followed it.

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The cast expanded well past the original four. Contemporary subjects including Bella Hadid, Kendall Jenner, and Adriana Lima joined the lineup, alongside a “Free Britney” canvas made the same year the #FreeBritney movement, the fan-led campaign challenging Britney Spears’s court-ordered conservatorship, was gaining mainstream traction, and mugshot portraits of design figures like Karl Lagerfeld. In a December 2020 interview, Toscano said he was going back to do a run of “legendary icons,” naming Steve McQueen, Paul Newman, and Sean Connery alongside Lagerfeld, and separately said he was developing a piece centered on Teddy Quinlivan, the first openly transgender model to walk for a major luxury house. It is unclear from available material which, if any, of those specific pieces were ultimately completed.

In September 2020, the mugshot format crossed over into pop culture entirely. Toscano wheat pasted a mask-awareness piece pairing Ryan Reynolds, styled as his Deadpool character, with Hugh Jackman, cast as Wolverine and booked, in the piece’s own joke, as the “Laughing Man Coffee Kingpin,” a nod to Jackman’s fair trade coffee company, Laughing Man Coffee. Both actors, who have run a long-running, good-natured public feud for years, shared the artwork on their own accounts. ComicBook.com and Cinemablend both covered the moment independently, and Jackman posted the Wolverine piece to his own account that January, tagging 1PENEMY directly.

A man in a blue mask and jacket takes a selfie in front of a poster featuring a mugshot of actor Ryan Reynolds wearing a blue mask, with a pink heart drawn over it.

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The premise Toscano describes for his own work, that fashion reduces women to interchangeable, endlessly reproduced images, sits in some tension with how that work has actually been produced and covered. The Soho Model Lineup depicts four women who did not commission or pose for it, rendered by a man working from photographs of patients and public figures. Whether that counts as pointed critique or simply another instance of the pattern it claims to criticize is a question none of the available interviews with Toscano ever really sit with.

The press record around 1PENEMY complicates the picture further. Most of the profiles cited here, including pieces published by Haute Living, Forbes India, and several smaller lifestyle sites, are explicitly labeled sponsored, partner, or brand-connect content rather than independent arts journalism, and much of the biographical detail about the art career, client lists, sale prices, and the reported $300,000 NFT run among them, traces back to a small number of nearly identical press bios distributed across those outlets rather than to reporting done independently of the artist. The mask campaign involving Reynolds and Jackman is the clearest exception, corroborated by outlets with no promotional relationship to Toscano and by the actors’ own social accounts. The dental biography holds up well against independent sources; the art career mostly has to be taken on the artist’s own word.

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Pricing across 1PENEMY’s output has moved with the medium, from the $350 signed print up to the five-figure canvases Gallery 23 NY now carries, with various profiles over the years citing overall ranges anywhere from roughly $1,000 to $25,000 depending on size and format. Toscano briefly entered the NFT market in early 2021, at the height of a boom that saw digital art sell for tens of millions of dollars at major auction houses, through the marketplace Portion, since shut down, which profiled him in an artist spotlight reporting an NFT run that raised more than $300,000 over eight days, a figure that comes from the platform’s own promotional writeup rather than independent verification. A separate NFT platform, Flipkick, listed a version of the work as a “physical NFT” priced at $15,000, describing its medium slightly differently, as mixed media acrylic rather than mixed media collage, a small discrepancy worth noting given how closely tied the piece’s value is to its billing as a unique, physical original.

Toscano has said a portion of proceeds from sold pieces goes to organizations including the Model Alliance and the Me Too Movement, both focused on protecting workers in the same industry his subjects come from, and he has spoken about donating art to charity auctions benefiting children’s hospitals and arts programs in New York. His work has also shown in group settings, including Gallery 23 NY’s 2021 exhibition “Stevie and Friends,” which ran June 3 through June 11 that year alongside street and pop artists Stevie Chow, Flore, and SeekOne. Whatever collection the Soho Model Lineup canvas eventually lands in, it remains what it was on the day it first went up on a wall in SoHo: a mugshot of an industry, made by a man who spends his days fixing that industry’s smiles.