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We can hear “Ol’ Blue Eyes” crooning “Send in the Clowns”, as we present this sketch by Frank Sinatra. Teamed with lyricist Sammy Cahn, Jimmy Van Heusen composed countless classic songs, including many hits recorded by Sinatra. A couple of the songs that were featured in Sinatra films won Best Song Oscars, with “All the Way” in the 1957 film “The Joker is Wild”, and “High Hopes” in the 1959 film “A Hole in the Head”. On top of the professional working relationship, Sinatra and Van Heusen were pals. Sinatra poked a little good-natured fun at Van Heusen, when he made this clown sketch on a menu at the well-known Sombrero Mexican Restaurant in Manhattan. This full page rendering is titled “James Van Heusen” at top, and the identifier “Francis Sinatra 77” is written at bottom-right. Due to a lack of exemplars, this Francis Sinatra name is not confirmed as being in Sinatra’s hand, though a letter of provenance accompanies from the son of a friend of Sinatra’s, who was gifted the sketch by Sinatra while having dinner with him and Van Heusen at the Sombrero restaurant. The artwork is consistent with another known clown sketch by Sinatra, who also painted clowns with some degree of skill. The offered menu remains solid with minor soiling on the front, and the Sinatra sketch is crisp and well-suited for framing.