Born in Fremont, Ohio, Holland began sending drawings to Walt Disney, as well as the Saturday Evening Post at the age of 15. At 17, after receiving a box of his drawings back from Disney with a Mickey Mouse masthead rejection letter as well as numerous rejection letters from the Saturday Evening Post, Holland traveled by bus to Chicago where he found odd jobs, including sweeping the floor of a tattoo parlor. At age 20 the artist was hired by Hallmark in Kansas City to illustrate books as a staff artist. Among the books he would illustrate for Hallmark was A Christmas Carol by Charles Dickens.In 1967 at age 23, Holland moved to New York City to pursue a career as a full-time freelance illustrator.
In 2008, Holland and fellow Illustration Partnership of America (IPA) board member Cynthia Turner submitted comments to The Committee on the Judiciary, regarding The Orphan Works Bill of 2008 and its potential threat to artist rights. While the bill did pass the Senate, and gained wide support in the publishing community it lost support in the House of Representatives and failed passage.
As an indirect consequence of the IPA involvement in the Orphaned Works Bill of 2008, the IPA was sued for one million dollars in 2008 for defamation by the Graphic Artists Guild (GAG), with Holland listed as the primary defendant. The GAG asserted claims for defamation and interference with contractual relations, alleging that IPA had interfered with a "business relationship" GAG had entered into that enabled GAG to collect orphaned reproduction royalties derived from the licensing of illustrators' work. GAG alleged that efforts by IPA to create a collecting society to return lost royalties to artists "interfered" with GAG's "business" of collecting these orphaned fees. Regarding a primary issue in the lawsuit: that GAG had appropriated over one and a half million dollars of illustrators' royalties "surreptitiously", the judge presiding over the case ruled that the statement by IPA was true, and that a defamation case could not go forward based on a statement of fact. The case against IPA and Holland was over-turned. In 2000 the GAG had awarded Holland the Walter Hortens Distinguished Service Award for his articles and speeches on the effects of stock illustration agencies on the freelance illustration business.
In 2012, the U.S Copyright Office engaged the Orphan Works issue again, specifically Orphaned Works and Mass Digitization. Holland and fellow IPA board Member Cynthia Turner once again represented the IPA by reiterating their earlier stance that copyright reform advocates are doing so because they wish to see nation's copyright wealth transfer from individuals to a few select corporations.
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