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. At The New York Times, Holland was brought in by Jean-Claude Suares, the first art director of the Op-Ed page and who is credited with bringing the first works of illustration to the editorial page of the New York Times. Holland's contributions to the Times Op-Ed page were seen as a fundamental shift in how illustration could be used in print, as more often than not Holland treated the art and text as two separate elements.
In 1969 Holland and Steven Heller founded the short-lived Asylum Press, created to represent and promote the work of artists and designers to underground and alternative press resources. After the failure of New York Review Of Sex, Heller became the art director of Screw: The Sex Review, for which Holland did some covers.
Holland's drawings, in particular those about the Nixon administration's Watergate scandal, became the single largest body of work to be published in the first book of Op-Ed art: The Art of the Times, edited by Jean-Claude Suares and published in 1973 by Darien House. In the same year, Holland would accompany Suares when the art director arranged an exhibition of Op-Ed art from The Times at the Musée des Arts Décoratifs in Paris.
By 1986, the artist was so firmly established as a prominent presence in the graphics community that The Washington Post said Holland was "the undisputed star of American Illustration". Writing for Print Magazine, Author Steven Heller wrote, "As Pollock redefined plastic art, Holland has radically changed the perception of illustration".
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