Sherman was born in Chicago, to Percy Copelon and Rose Sherman. Percy was an auto mechanic and race car driver who, like his son, suffered from obesity (he weighed over 350 pounds), and died while attempting a 100-day diet. His family was Jewish. Sherman's parents divorced when he was in grade school, and the son adopted his mother's maiden name.

One track from My Son, the Nut, a spoof of summer camp entitled "Hello Muddah, Hello Fadduh", became a surprise novelty hit, reaching No. 2 on the national Billboard Hot 100 chart for three weeks in late summer 1963. The lyrics were sung to the tune of one segment of Ponchielli's Dance of the Hours, familiar to the public because of its use in the Walt Disney film Fantasia. That December, Sherman's "The Twelve Gifts of Christmas" single appeared on Billboard's separate Christmas chart. Sherman had one other Top 40 hit, a 1965 take-off on the Petula Clark hit "Downtown" called "Crazy Downtown", which spent one week at #40. Two other Sherman singles charted in the lower regions of the Billboard 100: an updated "Hello Mudduh, Hello Fadduh" (#59 in 1964), and "The Drinking Man's Diet" (#98 in 1965). Sherman's "The End of a Symphony", spotlighting Arthur Fiedler's Boston Pops Orchestra, reached #113 on the "Bubbling Under" chart in 1964, but did not make the Hot 100.  The songs on Sherman's next album My Name Is Allan (1965) were thematically connected: except for a couple of original novelty songs with music by Sherman and Busch, all the songs on the album are parodies of songs that had won, or were nominated for, the Academy Award for Best Song. They included "That Old Black Magic", "Secret Love", "The Continental", "Chim Chim Cher-ee" and "Call Me Irresponsible". The cover of the album bore a childhood photograph of Sherman. That, and the album's title, were references to Barbra Streisand's album My Name Is Barbra, released earlier that year, which featured a cover photograph of the singer as a young girl.  During his brief heyday, Sherman's parodies were so popular that he had at least one contemporary imitator: My Son the Copycat was an album of song parodies performed by Stanley Ralph Ross, co-written by Ross and Bob Arbogast. Lest there be any doubt of whom Ross is copying, his album's cover bears a crossed-out photo of Sherman. One of the songs on this album is a fat man's lament, "I'm Called Little Butterball", parodying "I'm Called Little Buttercup" from Gilbert and Sullivan's operetta HMS Pinafore. Sherman would later parody this same song as "Little Butterball" - with the same subject matter - on his album Allan in Wonderland. The song may have had more poignancy for Sherman, as he, unlike Stanley Ross, was genuinely overweight. Sherman also parodied Gilbert and Sullivan's "Titwillow" from The Mikado, in the song "The Bronx Bird-Watcher" (on My Son, the Celebrity), as well as several other Gilbert and Sullivan songs.

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