In the history of old Hollywood, no romance was more storied than that of Katharine Hepburn and Spencer Tracy. Their romance was both touching and tragic. The older Tracy endured a troubled and restless childhood in the Midwest while Hepburn was well educated and raised in the lap of Connecticut old money. Tracy was abrasive and a binge drinker. Hepburn was fiercely independent and bossy. Yet somehow the stars aligned when they met on the set of “Woman of the Year” in 1941. Even the pair’s first words to each seemed to be lifted right out of a Hollywood script: "I fear I may be too tall for you, Mr. Tracy" said Hepburn, to which Tracy replied, "Don't worry, I'll cut you down to my size." Thus began one of the most unlikely romances in Hollywood history.
And even after their differences were overcome, proving opposites do indeed attract, the couple still faced the added hurdle of Tracy’s marriage. As a devout Catholic, divorce was out of the question, so the pair’s romance, though an open secret, would have to remain out of the spotlight. This inner conflict with his faith exacerbated Tracy’s propensity towards alcohol abuse and depression, but Hepburn remained by his side no matter what the circumstances. Publicly, the Tracy-Hepburn combination was wildly popular with movie audiences and the duo starred together in nine feature films. In the end, this ultimate “opposites attract” couple remained together for 26 years, parting only upon Tracy’s death in 1967. It wasn’t until 1983 when Hepburn spoke openly about her and Tracy’s two-and-a-half-decade relationship.
With their affair conducted behind closed doors and away from the public’s eye, there are precious few artifacts that remain to demonstrate the love and respect the two had for each other. This original drawing is one of those rare objects. Though Hepburn was known to paint depictions of her travels and the home she shared with Tracy, this is the only double-portrait known of the two together. The watercolor sketch by Hepburn is a double portrait with the love of her life. Painted two decades into their life together, the piece is a brutally honest look at the two. Hepburn depicts herself in angular strokes, her freckles, habitually hidden under layers of pancake makeup, are laid bare for all to see. Tracy’s furrowed brow shows the years of hard living behind him, yet the façade of his firm face is broken by his eye gazing admiringly at his partner. Executed in watercolor and ink on paper, the drawing measures 10 ¾” by 8 ½” and is signed in the lower right in black ink “Katharine Hepburn.” Originates from The Estate of Katharine Hepburn sale at Sotheby’s in 2004 where it sold for $66,000.

Estimate: $75,000+