Starting in 1958, Alan and three of his younger brothers (Wayne, Merrill, and Jay in their respective age orders) began singing as a barbershop quartet.

In 1962, the four Osmonds were cast over a seven-year period on NBC's The Andy Williams Show, a musical variety program They also appeared in nine episodes of the 1963–1964 ABC western television series, The Travels of Jaimie McPheeters, with Alan in the role of young Micah Kissel.

[3] During much of the Osmonds' career, Alan, being the oldest of the group, was the band's creative leader, playing piano and guitar, co-writing many of their songs with Merrill,[2] co-producing most of their recordings and arranging the dance choreography (he nevertheless seldom sang anything more than backing vocals, in contrast to his younger brothers).

[7] Osmond has credited his faith, and belief in the preexistence of the soul, for giving him hope and optimism for the future in the face of his condition.

[8] Prior to his marriage, Osmond dated extensively,[8] including a brief courtship with singer Karen Carpenter in the early 1970s.

[8] In 2000, Alan Osmond received the Dorothy Corwin Spirit of Life Award from the National Multiple Sclerosis Society.

In his acceptance speech, he stated that he had done some time in the military reserve and that he had taken karate lessons from Chuck Norris, both of which reinforced the "you can do it" attitude that he learned from his father.