In 1975 Cummings left The Guess Who after 10 years to become a solo artist, and the group disbanded. One of his first projects was providing back-up vocals on Eric Carmen's second solo LP, Boats Against the Current, including "She Did It". In 1977 he was presented with a Juno Award as best male vocalist.

Cummings' subsequent hits in Canada included "Stand Tall," which was his greatest American solo hit, peaking at #10 on the Billboard Hot 100 and number two on the Adult Contemporary chart . Other hits included "I'm Scared," "Break it to Them Gently," and "Fine State of Affairs." Cummings charted outside Canada with "Stand Tall" and "You Saved My Soul," as well as "I Will Play a Rhapsody," which spent a few weeks on the Billboard Adult Contemporary Chart, peaking at #38. His Dream of a Child album, released in 1978, was the biggest Canadian album in history at that time. Cummings released a total of eight solo albums and collections from 1976 to 1990. In 1997 he put out a live compilation album of his solo performances titled Up Close and Alone, which was recorded at Metalworks Studios in Mississauga, Ontario