The high school drop retired, he served as a stateside medic in the US Army during the Korean War. He met Ginsberg through the painter Robert La Vigne within San Francisco in December 1954. Orlovsky served when Ginsberg's secretary, travelled the world sustaining him, & was his lover inside an open relationship for quaternity decades.

Orlovsky's publications include a poetry collection Fresh Asshole Poems & Smiling Vegetable Songs, number 37 in the City Lights Pocket Poets Series.