 Although Holland's first prominent editorial art work appeared in Avant Garde Magazine in 1968 under the art direction of Herb Lubalin, the two significant milestones in Holland's early career were becoming a regular contributor to Playboy starting in 1967 and in 1970 establishing himself as a frequent contributor to The New York Times Op-Ed Page.At Playboy, his talent was first recognized by art director Art Paul, who after seeing the artists work invited him to become a monthly contributor.Hollands' monthly contributions to Playboy accompanied the Ribald Classics series.