Thomas Hart Benton's TP and Jake is to lead the auction of Simpsons co-founder Sam Simon's art collection.
The work is expected to make around $1.5m-2.5m.
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Simon, who died earlier this year, was an avid collector - particularly of work by American artists. His collection will be sold across a series of sales this year.
The proceeds will go to the Sam Simon Foundation.
Other pieces include Val Veeta, a work by pin-up artist Mel Ramos that carries an estimate of $400,000-600,000.
Andrea Fiuczynski, chairman of Sotheby's west coast division, comments: "Each piece in Sam Simon's collection embodies a central theme: the ability of art to tell a story.
"It is a privilege to present a window into the life of such a prolific creative talent. His own story lives on through his extensive cultural and philanthropic contributions, and we are particularly honored to see his collection benefit his namesake foundation."
Various rare pieces of Simpsons memorabilia will appear alongside the art, including a pinball machine that's valued at $2,000-3,000.
Simon was instrumental in the development of the show, which remains the longest running American sitcom in history.
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