BEVERLY HILLS, CA.- To many collectors, certain fine art lots can carry significant value when they were created on the cusp of an artistic breakthrough. Such is the case with Cy Twombly's 1956 Portrait of Henry Heymann (est. $100,000-150,000), which is expected to be one of the most in-demand lots offered at Heritage Auctions' Modern & Contemporary Art Auction Nov. 30 in Beverly Hills, California.

Twombly and Heymann (the sitter) became close friends when Twombly was a young art teacher at Southern Seminary Women's College in Lexington, Virginia, and Heymann was an undergraduate at nearby Washington and Lee University. The bond between the two was instantaneous, inevitable and lasted for decades as each man gained artistic notoriety.

Painted in 1956, this large (45-by-33-inch) oil-and-graphite-on-canvas portrait exhibits Twombly's gestural style and emerges from a notable time in Twombly's personal life and evolution as an artist. A year later, Twombly married Italian baroness Tatiana Franchetti and moved to Rome, where he fully developed his signature sgraffito style and emerged as an important Modernist painter. While much of the focus of the art world was shifting from Europe to New York, Twombly's decision to move permanently to Italy at the moment of his emergent fame revealed his go-against-the-grain personality and artistic autonomy.

A 1958 airmail letter and envelope from Twombly in Rome to Heymann in the United States accompanies this portrait in the lot. Indeed, Heymann did visit Twombly in Rome several times over the next decades and kept this portrait in his private personal collection for 61 years, until its auction offering in Beverly Hills Nov. 30.