Burt Britton's hobby began in the mid-1960s with Norman Mailer while Britton was bartending at the legendary Village Vanguard. The author was the last customer late one night and was refusing to leave, according to the auction catalog's notes.
"What do you want from me, kid?" Mailer repeatedly asked.
Britton says he finally handed the Pulitzer Prize writer a piece of paper and told him, "Do a self-portrait for me, drink your drink, and let's call it a night."
He doesn't know why he made such a demand, but that "began all this madness" -- a decades-long collection of mostly quick, ink-on-paper drawings from the famous and soon-to-be famous, Britton says in the notes.
Bloomsbury Auctions in Manhattan will offer 213 lots of the self-portraits on Thursday. Some are crude and funny caricatures; others depict a close likeness to the subject.
Mailer's abstract angular profile with curly hair is expected to bring $2,000 to $3,000.
"Rarely do you get to see authors looking inward this way and expressing themselves in drawings, let alone making portraits of themselves," said Bloomsbury rare books and manuscript specialist Peter Costanzo.
Also interesting, he said, are the sketches by artists and photographers who identified themselves with the tools of their trade. Photographer Andre Kertesz, for example, drew himself as a camera with a single human eye and inscribed it, "I am the camera."
Britton's later jobs at Strand Book Store in Lower Manhattan, where he was vice president for 10 years, and Books & Company on Madison Avenue as co-owner both afforded him opportunities to meet celebrated authors.
Capote, the author of such classics as "In Cold Blood" and "Breakfast at Tiffany's" depicted himself with a perfectly round face, round eyeglasses and one line for the nose and another for the lips. It's estimated at $2,500 to $3,500.
The sketch by Abdul-Jabbar -- a simple stick figure -- was obtained when the basketball great was still in high school but already a legend then known as Lew Alcindor.
Abdul-Jabbar was in line at the Vanguard, Britton says, on a night when he was working the door.
"I told him to forget the line and go around to the back door," says Britton. He concedes that Abdul-Jabbar was "a bit underage" so he told him that his price of admission would be a self-portrait. It's estimated to sell for $400 to $600.