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 (Dec. 27), 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.
Sheldon also provided the voice for the Conjunction Conductor and performed as proposed legislation in the memorable piece “I’m Just a Bill” on the Saturday morning kids educational series Schoolhouse Rock!, which premiered on ABC in 1973.
He parodied “I’m Just a Bill” as an “Amendment to Be” on an 1996 episode of The Simpsons and reprised his roles as the bill and the conductor on episodes of Family Guy in 2000 and 2001.
Sheldon was born on Nov. 30, 1931, in Jacksonville, Florida, and began playing trumpet at age 12. He moved to Los Angeles in 1947, attended L.A. City College and studied with Uan Rasey, then played with military bands in the U.S. Air Force and, after the service, with the likes of Jimmy Giuffre, Dexter Gordon and Chet Baker.
In the late 1950s, Sheldon toured with orchestras led by Stan Kenton and Benny Goodman and backed Rosemary Clooney, Peggy Lee, Sammy Davis Jr., Frank Sinatra and other vocal superstars. 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.
An inventive player, he also headed his own 17-piece orchestra.
As as actor in the 1960s, Sheldon portrayed 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. A spoof of The Fugitive from Get Smart producer Leonard Stern, it lasted just 13 episodes.
He then played the brother of John Davidson’s character on the 1973-74 NBC sitcom The Girl With Something Extra, starring Sally Field, and appeared in Freaky Friday (1976) and on episodes of Mike Hammer, Private Eye.
Sheldon also was the voice of Louie the Lightning Bug in a series of musical cartoon PSAs in the 1980s and performed the theme song for the 1990’s ABC series Homefront, starring Kyle Chandler.
Sheldon was the subject of a 2008 documentary, Trying to Get Good: The Jazz Odyssey of Jack Sheldon, in which he detailed his battle with alcohol and substance abuse. He then made a resounding recovery from a stroke suffered in 2011 that robbed him of the use of his right arm.
“I like the music to swing,” he told the Los Angeles Times in 1987, “and I like to make people feel it, feel happy and sad, everything. If the music makes me smile and happy, then maybe the people will feel it, too.”
A memorial service is scheduled for 2 p.m. on Jan. 10 at Forest Lawn in Cypress, California.
This article originally appeared on The Hollywood Reporter.