According to The Hollywood Reporter, the extraordinary West Coast jazz trumpeter, Jack Sheldon died Friday at the age of 88 years old.  He was also the singer in “The Shadow of Your Smile” for the big screen, as well as served as Merv Griffin’s sidekick and voiced characters on Schoolhouse Rock!

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).

On Griffin’s popular TV talk show, which started in 1962, Sheldon was prominently featured for 16 years before being hired for Mort Lindsey’s band and enjoyed rich comic banter with the host, a big band singer himself. Sheldon performed Griffin’s favorite song, “The Shadow of Your Smile,” at Griffin’s funeral in 2007.

Sheldon also lent his voice for the Conjunction Conductor and also performed as legislation in  “I’m Just a Bill” on an episode of Schoolhouse Rock! a popular Saturday morning kids educational series that premiered in 1973 on ABC.

Years later he would parody “I’m Just a Bill” as an “Amendment to Be” for a 1996 episode of The Simpsons and then  reprised his roles as both the bill and the conductor on episodes of Family Guy in 2000 and 2001.

Born on Nov. 30, 1931, in Jacksonville, Florida, Sheldon started playing trumpet around the age of 12. In 1947 he moved to Los Angeles and attended L.A. City College where he studied with Uan Rasey.  From there he played with military bands in the U.S. Air Force and, after the service, with such notable names as Jimmy Giuffre, Dexter Gordon and Chet Baker.

Throughout the 1950s, Sheldon toured with orchestras led by Stan Kenton and Benny Goodman and backed Rosemarie Clooney, Peggy Lee, Sammy Davis Jr., Frank Sinatra and others. He also played with Herb Geller, Art Pepper, Wardell Gray, Dave Pell, Curtis Counce, Woody Herman, Al Porcino, Bill Berry, Maynard Ferguson and Buddy Childers.

He was an actor throughout the 1960s, portraying neighbor and jazz musician Fletcher Kincaid on The Cara Williams Show and starred as Buddy Overstreet, a young accountant on the run from gangsters, on another CBS series, Run, Buddy, Run. Also, a spoof of The Fugitive from Get Smart producer Leonard Stern, that lasted for only 13 episodes.

A memorial service is scheduled for 2 p.m. on Jan. 10 at Forest Lawn in Cypress, California.