Oliver Frey was born in Zurich, Switzerland on 30 June 1948. He grew up fluent in Italian and German. His family moved to Britain in 1956 but subsequently returned to Switzerland.
During his high school years in Switzerland, Frey followed an American correspondence course called The Famous Artists.
After spending six months in the Swiss army, and dropping out of Berne University, Frey moved to Britain once again and started a two-year course at the London Film School during which he supported himself with freelance work, including drawing historical illustrations for the War Picture Library.
As a child Frey loved The Eagle comic, and as an adult was able to fulfil his childhood dream by working on the revived version, drawing the strip Dan Dare. Also during the 1970s, he illustrated for IPC Media's Look and Learn magazine, including the strip The Trigan Empire.
When his brother Franco founded the computer magazine CRASH in 1983, together with Roger Kean, Oli became the magazine's illustrator. He also illustrated CRASH's sister magazines Zzap!64, Amtix and The Games Machine. Many of the Crash/Zzap! 64 covers, especially the earlier issues, had a clear homoerotic flavour to them, with pictures of (predominantly) bare chested youths, which had, at most, only a tenuous relevance to the magazines content.
Through the late 1970s and the 1980s Frey was a prolific creator of gay erotic art including a series of a Tom of Finland-style bad-boy hero named "Rogue" for Him Magazine, and has produced, edited and illustrated several issues of Man-to-Man Magazine.