Not just anyone can shack-up in the Hotel Chelsea. Reserved for the oddest, craziest, most brilliant cream of the creative crop, its rooms have housed everyone from Mark Twain to Jack Kerouac, Willem de Kooning to Marilyn Monroe, Sarah Bernhardt to Sid Vicious. So the fact that legendary manager and curator of residents, Stanley Bard, chose Sam Bassett as the artistic haven’s last permanent tenant is no doubt a testament to his evolving talents.

With long blond locks and a lackadaisical yet pensive demeanor, the 31-year old Bassett is some curious combination of a 90s skater-renegade and a sagely old-world philosopher. His unconventional portraits and fashion photography have been featured in publications like The New York Times and GQ. His geometric tape sculptures are stuck upon New York’s billboards, walls and windows, and his short films have been screened at festivals around the world. But his most recent endeavor, a series of seven feature films, is undoubtedly his greatest feat to date.

Bassett’s cinematic voyage began in 2006 whilst sitting in the East Village’s Tompkins Square Park. Approached by a charismatic “cowboy” who’s relationship with reality is still in question, Bassett was instantly struck by his quick-witted elocution, tangled beard and signature cowboy hat:

“The way he spoke, the way he formulated his sentences, his charm and his intellect, I found it very unique and very interesting,” said Bassett. So interesting that he chose the quirky New Yorker as the subject of his first feature-length film, Cowboy Stan. A comedic and disturbing journey through alcohol-induced meltdowns, endearing country-music sing-alongs, and  fleeting moments of prolific clarity, the film documents this native New York cowboy during the two weeks leading up to his birthday. While their time together was brief, the filmmaker hoped that it would be “enough to tell his story – or a story – to make people feel and to inspire people.”

Through infiltrating Cowboy Stan’s unlivable apartment, lonely existence and ultimately his psyche, Bassett’s beautifully raw filming techniques explore a realm of the human condition that most of us are unwilling to acknowledge.

Bassett’s Cowboy Stan experience spawned a series of six additional films, all of which fit together to explore uncovered truths, the intricacies of humanity and marginal histories that seemed destined to be forgotten. By combining pure documentary and choreographed metaphors, the films crack open and pay tribute to the lives of eccentric elders ranging from Stormé DeLarverié, a bi-racial civil rights leader who threw the first punch at the Stonewall Riots to a Hollywood conman who refers to himself exclusively as “Columbia.” Each character embarks on a journey. Each character gains something. And most importantly, each character experiences powerful realizations about their past, present and future. 

Bettina, the second film in the series, is perhaps the most extraordinary of the seven stories. After thirty years of seclusion, artist and Hotel Chelsea resident Bettina Bashyi undergoes a complete renaissance of mind, body and spirit via her friendship with Bassett. Formerly known as “the most beautiful woman to ever live in the Hotel Chelsea,” Bettina’s cluttered apartment has been deemed a fire hazard. Bassett tirelessly clears away more than a quarter-century of clutter and, in the process, discovers Bettina’s astounding works of art and truly amazing past. Brought together by what Bassett describes as “cosmic consciousness,” the filmmaker was attracted to Bettina’s “deep creative understanding,” mystical thinking and complex philosophies. And while due to snubs from the art world and personal demons, her life may not appear to be a conventional success, Bassett believes that it makes for a “more beautiful story.”

Constance, a tribute to Constance Colt Bassett, the filmmaker’s 94-year-old grandmother and muse, is another poetic highlight in the series:

“I wanted to show the legacy of this very great, very dignified, very centered  woman who has always been a great inspiration and love of my life as my grandmother and a friend,” revealed an emotive Bassett.

A refined pistol with a passion for horses and after-dinner drinks, Constance travels to her Geneseo, New York childhood estate and experiences an intense recollection of her former life as a young woman. We see her wisdom, worldliness and marvelously cutting wit as she takes a journey through time and experience. The film is an ode to storytelling and its elegant cinematography more than adequately celebrates the woman Bassett calls Granny. 

The series ends with Stanley Bard, a film that celebrates not only the iconic Hotel Chelsea, but the man who, for half a century, fostered the Hotel as a “creative ecosystem,” for some of the greatest minds of our time. Considering the Hotel’s essential role in this series of films, in Bassett’s artistic career and in the lives of many of his subjects, it’s only appropriate the series will be screened this week on the roof of the Hotel Chelsea.

When asked what common thread holds these philosophical films together, Bassett responded:

“Truth. Truth and love, I would say. And a journey. The journey of life. The journey of one’s spiritual understanding. All the films are different types of people but one can garner little bits of knowledge and perspective from all of them to be able to hopefully grow and learn and make the world a better place. “

It might sound cliché, but after experiencing the journeys of Bassett’s subjects, and more importantly, witnessing the artistic and personal evolution of Bassett himself, it’s difficult to walk away with an unaltered perspective.

To view the trailers, visit Bassett’s website.  The films will be screening for the next seven nights (July 20-26) on the roof of The Hotel Chelsea (222 W.23rd st.). Each screening opens with a cocktail reception from 8:00 to 9:00 PM. One film will be screened each evening starting at dusk or approximately 9:36 PM, A brief audience Q&A with the director and subject following the screening. To RSVP for the event, email alainasimone@sambassett.com and rsapla@groupsjr.com.