Greg was born in Manila and grew up in the Far East. He was educated at Sedbergh in the United Kingdom, traveled in Europe and finally came to the US. His first instructor was the Filipino genre artist Gabriel Custodio. Before he left the Philippines Greg's first exhibits were at the Phil Am Life Bldg and the Philippine National Library.

In 1966 Antonio Ma Nuevo of the Philippines Herald wrote:"Almost brutally consistent in his fifty drawings and paintings, done with the greatest of ease on board or canvas." In the US he studied at the Honolulu Art Academy, the California College of Arts and Crafts and the San Francisco Art Institute where he received his B.F.A.

For much of the seventies he worked as a still photographer for a variety of now defunct West Coast publications that read like a memorial of another time: Ramparts, Earth, Berkeley Barb, Vanguard, Good Times as well as Andy Warhol's Interview, the New York Post and Actual.

Moving to Chicago, Greg Pickup became a grain speculator (speculari—to spy out or examine) and was a member of the Chicago Board of Trade from 1979 to 1986.

In 1989 he exhibited at Galleria Renata—"Chicago Board of Trade trader, Gregory Pickup imbues his canvasses with raw untempered emotion," wrote Silvino da Silva. He also exhibited at the Sybil Larney Gallery in Chicago.

In the 90's Pickup joined the Palette and Chisel Academy in Chicago to return to work based on direct observation of the human figure. During this period he illustrated the cookbook, "Eat Like a Horse" (And lose Weight) and wrote and illustrated the financial parable "The Trouble with Bubbles." In his review, Robert Prechter of the Eliott Wave Theorist, wrote, "This wise send-up of stock mania is a hoot."