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E. Leonard Rubin passed away on February 3, 2026, at age 93. Born in Chicago to Frances Rabin and Samuel Rubin on January 11, 1933, “Lenny” was the youngest of three (sister Inez and brother Sheldon).

After serving in the Army, Lenny completed his undergraduate and law degrees at the University of Miami and moved to New York, where he saw as many Broadway plays and Leonard Bernstein concerts as he could, before moving back to Chicago.
Len practiced copyright and entertainment law. He was General Counsel of Playboy, and had an illustrious career representing authors, playwrights, musicians, photographers, filmmakers, artists, reporters, journalists, and more.

Lenny was a pillar in the Chicago legal community. For decades he was the Director and head writer of the Chicago Bar Association’s annual “Christmas Spirits” show. At the helm of the “Bar Show,” Len created a heyday of political satire in Chicago, drawing attendance from governors, mayors, judges, and everyone who was anyone in the legal or political community. The Bar Show was a place to see and be seen, thanks to the tireless efforts of Len and his friends. “Road show” performances across the country earned accolades as well, including from U.S. Supreme Court Justice Douglas.

It was in his role as Director of the Bar Show that he met his wife, Audrey (née Holzer). The two shared a mutual love of the law, theater, music, and travel. Over their 43 years together, they traveled around the world, often with their two daughters Margot (Zeke Sulkes) and Bette, performed together in the Bar Show in Chicago, and sang with the Yale Alumni Glee Club in England, Wales and Russia, as well as at Carnegie Hall. They made countless trips to New York and London to see shows, and never tired of watching their favorite classic movies such as Casablanca and Airplane!

An active member of the Copyright Society of the USA, Len enjoyed everything “entertainment law.” He mentored young lawyers, taught Entertainment Law at John Marshall/UIC Law School, and presented at numerous symposia. He wrote articles for copyright and entertainment books and treatises, and gave interviews as an expert on issues ranging from the rise of illegal music downloads in the early 2000s to the famous “monkey selfie”. He was a tremendous writer, from impeccable legal briefs at the first draft, to chronicling his life story, always with a profound sense of wit and heart. To know Lenny was to love him. His stories captivated everyone within earshot, and his sense of humor was unparalleled.

Len leaves behind his wife, Audrey (nee Holzer), daughters Margot (Zeke Sulkes), Bette, Suzanne, son Matthew (Anne Brady Rubin), grandchildren Ezra Sulkes, Mabel Sulkes, Keaton Rubin, and Maeve Rubin.

In lieu of flowers, the family kindly requests donations be made to either Temple Beth-El of Northbrook or the Gastrointestinal Research Foundation (GIRF).