Clemenson was born and raised in Humboldt, Iowa, the son of drug store owners Ruth Alzora (Dayton) and Ernest Arnold Clemenson. In his early teens, he delivered the Des Moines Register, which had a long tradition of awarding scholarships to top east-coast preparatory schools to a select few "paper boys." Clemenson, a straight-A junior high school student, won a Register scholarship to Phillips Academy in Andover, Massachusetts. In 1973, while Clemenson was enrolled at Phillips, his father died at age 58. He participated in many theatrical productions at Phillips Academy.
Upon graduation from Phillips in 1976, he entered Harvard College. From his freshman year onward he received important roles in campus stage productions. When Clemenson starred in a Harvard Lampoon sketch comedy show, a Harvard Crimson theater critic described Clemenson as "hugely talented actor who can trigger hysteria with any of a dozen subtle expressions or inflections." Other Crimson critics described his performances in Shakespeare plays as "a tour de force of sheer talent and intelligence" (in The Winter's Tale) and "a very fine and subtle performance" (in Measure for Measure). He displayed early on his remarkable range when he undertook with inimitable flair and hilarious effect the hugely solemn role of Erde "the green-faced torso", goddess of the Earth, in Peter Sellars's Loeb Drama Center puppet production of Wagner's Ring cycle (1979).[citation needed]
During many summers he would return to Humboldt to star in, and later direct, local community theater plays at Humboldt's Castle Theatre.

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