John Berg–the Grammy-winning art director for Columbia Records who was responsible for some of the most recognizable album covers of the 20th century–died Sunday at the age of 83, according to the New York Times . The cause of death was pneumonia.

Over the course of his career, Berg designed more than 5,000 albums for artists as well-known and wide-ranging as Bob Dylan, Thelonious Monk, Blood, Sweat & Tears, and Barbra Streisand.

Born and raised in Brooklyn, Berg graduated in 1976 from Cooper Union with a bachelor of fine arts. After a brief stint designing packaging for Pepsi, he worked various jobs in advertising and editorial, for companies like Grey Advertising and Esquire. After joining Columbia in 1961, Berg went on to become a 29-time Grammy nominee, ultimately winning four.

Berg will long be remembered for his wit, inventive typography, and frequent use of gatefold covers. As a Co.Design tribute, we’re revisiting the stories behind four of his most famous cover designs.

Columbia Records

Bob Dylan’s Greatest Hits

Featuring a backlit photo of Dylan performing, Bob Dylan’s Greatest Hits is among the best-known covers designed under Berg’s direction. In one of the first examples of music marketing, Berg commissioned Milton Glaser to design the now-iconic psychedelic Dylan poster. “Dylan hadn’t had any product out in a while. So we decided that it would be nice for the consumer to give them a little bonus,” Berg wrote in a piece for Cooper Union. “It was the first time a poster was ever enclosed in an album. I picked Glaser because he had a big reputation as a poster artist.”

Columbia Records

Big Brother And The Holding Company’s Cheap Thrills

Big Brother and the Holding Company’s 1976 album Cheap Thrills features illustrations from the counterculture cartoonist R. Crumb, who was famously against “commercial” work of any kind. “[Janis] Joplin commissioned it, and she delivered Cheap Thrills to me personally in the office,” Berg told design professor Paul Nini in an interview for AIGA. “There were no changes with R. Crumb. He refused to be paid, saying, ‘I don’t want Columbia’s filthy lucre.'”

Columbia Records

Chicago

Berg’s design for Chicago’s cursive logo was partially inspired by Coca-Cola. Over the course of several albums, the logo appeared in wood, leather, the ridges of a fingerprint, and printed on a sepia-toned map. In 1976, for Chicago X, Berg molded the logo in chocolate, an idea that later earned him a Grammy.