Few creators have matched the breadth of Shel Silverstein, who thrived simultaneously as composer, singer, cartoonist, illustrator, and author while scoring popular triumphs in every field. Sheldon Alan Silverstein entered the world in Chicago in 1930. During his military stint in Japan and Korea he first gained attention by contributing cartoons to the armed-forces newspaper Stars & Stripes. Once back in civilian clothes he earned part of his income vending hot dogs at Chicago’s two ballparks; a 1961 publisher’s note claimed he set a sales record for Thursday-night games. He also began placing drawings in Look, Sports Illustrated, and This Week, yet national recognition arrived only after he joined Playboy in the mid-1950s. The magazine stood at the forefront of postwar culture, and Silverstein’s cartoons—running in every issue from 1957 into the mid-1970s—delivered some of its sharpest satirical and provocative commentary.
By the late 1950s Silverstein was extending his reach into writing and music as well. His debut LP, Hairy Jazz, appeared on Elektra Records and mixed two original numbers with vocal interpretations of several jazz standards. That release inaugurated a recording career that ultimately spanned more than two decades and crossed every genre. The follow-up, Inside Folk Songs, offered a biting comic portrait of the early-1960s folk revival and contained the first version of “The Unicorn Song.” Three further albums came out on Chess’s forward-looking Cadet imprint. While continuing his magazine illustration work, he issued cartoon collections in book form—Now Here’s My Plan (Simon & Schuster) and Grab Your Socks (Ballantine)—and published the children’s title The Lion Book. Regular radio appearances followed on The Jean Shepherd Show, where he performed as musician and actor, and he joined Roger Price as a recurring television presence. He also took the stage as singer and banjoist with Papa Bue’s Danish Viking New Orleans Jazz Band and as a solo performer.
Alongside literary successes such as the children’s volumes Uncle Shelby ABZ Book, Uncle Shelby’s Zoo, and Giraffe and a Half, Silverstein established himself as a sought-after songwriter. Early cuts of his material by Bob Gibson and Hamilton Camp—“The First Battalion” and “You’re Wasting Your Time Trying to Make Me Settle Down”—appeared in the early 1960s, yet “The Unicorn Song” achieved independent life once the Irish Rovers transformed it into a major international hit. The Brothers Four scored with his “25 Minutes to Go,” but 1967 brought genuine songwriting stardom when Johnny Cash’s rendition of “A Boy Named Sue” became a massive success. RCA promptly released an album of Silverstein’s songs under that title. The most consequential and commercially strongest album of the period, however, was 1973’s Freakin’ at the Freakers Ball, which trained its sardonic gaze on the counterculture, hippies, and every stripe of radical. A year earlier “Sylvia’s Mother,” an extravagant romantic lament, climbed to number five and launched Dr. Hook & the Medicine Show; the band, which also played on Freakin’ at the Freakers Ball, scored an even bigger hit with the satiric “The Cover of the Rolling Stone,” likewise penned by Silverstein. For the remainder of the 1970s the group served as the principal outlet for his material. Another track from the 1973 album, “Don’t Give a Dose to the One You Love Most,” later became a theme for various anti-venereal-disease campaigns.
Even while sophisticated listeners prized his adult-oriented satire, Silverstein remained a best-selling children’s author whose titles included Falling Up (1996), The Missing Piece (1982), Where the Sidewalk Ends (1981), A Light in the Attic (1981), and, most enduringly, The Giving Tree (1964), which stayed in print for nearly four decades. In 1983 his play Wild Life premiered off-Broadway to enthusiastic notices, and he received an Oscar nomination for the song “I’m Checking Out,” written for Mike Nichols’s 1990 film Postcards from the Edge. Additional Silverstein compositions appeared in Ned Kelly, Coal Miner’s Daughter, Hearts of Fire, and Things Change. The artist’s singular career ended when he suffered a fatal heart attack at his Key West home in May 1999.
