Wolin attended the University of Wyoming and then was graduated from Art Center College of Design in Pasadena, California, majoring in photography and film.
The hotel, on the corner of Hollywood Boulevard and Western Avenue, sheltered a range of people from all ages and walks of life, staying from one night to thirty years.
Jewish-American photographers interviewed and photographed by Wolin include Lillian Bassman, Jo Ann Callis, Lauren Greenfield, Elinor Carucci, Lois Greenfield, Bruce Davidson, Annie Leibovitz, Herman Leonard, Helen Levitt, Jay Maisel, Joel Meyerowitz, Arnold Newman, Robert Frank and Joel-Peter Witkin.
Posthumous interviews include the families of Philippe Halsman, Herb Ritts, Nickolas Muray, Arthur Rothstein, Roman Vishniac and Garry Winogrand.
Traveling during each season throughout Wyoming, Wolin photographed and interviewed the native and newly arriving residents, ranging from cowboys to oilfield roughnecks to elected officials.
Captioned in a way that is at once playful and exacting, and coupled with a brief essay that collapses the space between what Wolin calls 'existential Hollywood' and the actual place, these portraits show the opposite of what you might expect: a world in which dreams may be diminished but their originators, these noble occupants of the St. Francis Hotel, are radiant, beautiful, timelessly alive.
Wolin lived there for three weeks to document its residents — a mix of misfits and dreamers, transients, artists and adventurers — for a photography project at ArtCenter College of Design."
[9] The New York Times, California Today: Mike McPhate writes, "In the charred rubble of Santa Rosa it was the McDonald's that drew Penny Wolin, a photographer who lives nearby.
In Descendants of Light: American Photographers of Jewish Ancestry (Crazy Woman Creek Press, 244 pages) she has testimony from or about Diane Arbus, Richard Avedon, Bruce Davidson, Philippe Halsman, Annie Leibovitz, Helen Levitt, Rosalind Solomon, Alfred Stieglitz, and more than 60 others.
"[14] University Press of Mississippi, Through the Lens of the City: NEA Photography Surveys of the 1970s: In an interview with Mark Rice, Wolin notes, "Wyoming was not inundated with the mass American culture.
A press release from the Wyoming Council on the Arts noted that Wolin's central concern was "the final and inevitable assimilation of the Old West into the American culture."
"[16] San Francisco Chronicle, Jon Carroll writes, "She had a wonderful way with black and white portrait work, and a loving approach to her subjects...in my mail arrived a splendid book called The Jews of Wyoming: Fringe of the Diaspora.
[18] The Washington Post, At National Museum of American History: Sarah Booth Conroy writes, "Going through the exhibition takes time as the viewer tries to understand the text and the photographs, both works of art.
"[20] Los Angeles Times, Art Review: 'Hollywood' Resembles A Cutting-room Floor, Colin Gardner writes, "The show's one saving grace is its photography, in particular Penny Wolin's Diane Arbus-like Guest Register (1975), a poignant yet devastating documentation of the residents of the St. Francis Hotel near the Hollywood Walk of Fame.
Combining image and text, Wolin's examination of life's lost souls and anonymous citizens who are just passing through manages to be both emotionally distanced without being condescending.
"[21] American Photographer magazine, Getting a Grip on Hollywood: David Roberts writes in his feature article, "She is...a methodical, quiet professional who uses large negatives, poses her subjects carefully and concentrates on details...