After working as a senior editor at the Village Voice, editing the paper's political and news coverage and writing a cover story exposing the corrupt politics behind the proposed redevelopment of Times Square, his interests for lost causes led him to New York Newsday, where he wrote a weekly media column and covered the 1988 presidential campaign.

[2] In 2001, Guttenplan's interest in the uses of British libel laws to silence criticism led him to write about the suit brought by British author David Irving, who claimed no Jews were killed in gas chambers at Auschwitz, against American academic Deborah Lipstadt, who had called Irving "one of the most dangerous spokespersons for Holocaust denial."

Guttenplan's account of the case, The Holocaust on Trial, was described by Ian Buruma in The New Yorker as "a mixture of superb reportage and serious reflection—about the role of Jewish identity politics in the United States, antisemitism in Britain, the historiography of the Cold War, and so on.

[7][8] The British journal Sight and Sound described the film as "the kind of portrait of an intellectual which is very rare," while The Times of London called it "enthralling, touching, melancholic and fierce."

The New York Times pronounced it "riveting", adding "Edward Said: The Last Interview proves that a couch, a camera and a great mind can be all the inspiration a filmmaker needs.