He also voiced singing characters on ‘Schoolhouse Rock!’ and was an actor on the 1960’s comedy ‘Run, Buddy Run.’

Jack Sheldon, the extraordinary West Coast jazz trumpeter and singer who played “The Shadow of Your Smile” for the big screen, served as Merv Griffin’s sidekick and voiced characters on Schoolhouse Rock!, died Friday, his longtime manager, Dianne Jimenez, reported. He was 88.

Sheldon performed the haunting “The Shadow of Your Smile” on the Elizabeth Taylor-Richard Burton drama The Sandpiper (1965), and the tune, written by Johnny Mandel and Paul Francis Webster, won the Grammy Award for song of the year and the Academy Award for best original song.

He also played one of the many versions of “The Long Goodbye” on Robert Altman’s 1973 classic that starred Elliott Gould as Philip Marlowe and was heard and/or seen in other films including Breakfast at Tiffany’s (1961), Save the Tiger (1973), The Killing of a Chinese Bookie (1976), Mommie Dearest (1981), Mr. Saturday Night (1992), Arachnophobia (1990) and For the Boys (1991).

Tony Gieske, the late jazz reviewer for The Hollywood Reporter, once described Sheldon’s “incomparable trumpet sound” as “rich and full as something I wish I could think of to compare it to — a bunch of dewy green grapes?”

On Griffin’s long-running TV talk show that began in 1962, the fun-loving Sheldon was front and center for 16 years after being hired for Mort Lindsey’s band and enjoyed rich comic banter with the host, a big band singer himself. Griffin’s favorite song was “The Shadow of Your Smile,” and Sheldon performed it at Griffin’s funeral in 2007.

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