Guttentag won an Oscar for Best Documentary with his HBO film You Don't Have to Die, telling the story of one boy's battle against cancer. Guttentag would receive three more Oscar nominations before winning another Oscar for his 2003 documentary Twin Towers.
In 2007, Guttentag directed two films – Live!, which premiered at Tribeca Film Festival, starring Eva Mendes, Andre Braugher David Krumholtz, Jeffrey Dean Morgan and Jay Hernandez; and Nanking, which premiered at the Sundance Film Festival, a documentary about the Rape of Nanking during World War II. Nanking featured Woody Harrelson, Mariel Hemingway and Jürgen Prochnow. Nanking was shortlisted for an Academy Award, won awards at Sundance Film Festival and other film festivals, earned Guttentag a Writers Guild of America Award nomination, and went on to become the highest grossing theatrical documentary in Chinese history. Nanking also won an Emmy Award and a George Foster Peabody Award in 2009.
Live! had its American premiere at the Tribeca Film Festival and its international premiere at the Deauville Film Festival, and was distributed in the US by The Weinstein Company. Its international distribution included Lions Gate Entertainment (UK) and Pretty Pictures (France).
Guttentag's films have been selected for Sundance three times, Tribeca four times, and have won awards at numerous American and international film festivals. They have also received a number of special screenings internationally and in the US, including at the Museum of Modern Art in New York, the Harvard Kennedy School, and the White House.
Guttentag has received three Emmy Awards, two additional Emmy nominations, two Writers Guild Award nominations, a Producers Guild Award nomination, and a Robert F. Kennedy Journalism Award.
Guttentag has been a lecturer at the Stanford Graduate School of Business since 2001. He also teaches at the Hasso Plattner Institute of Design at Stanford (d.school).
His film Only the Dead See the End of War premiered at the 2015 Telluride Film Festival and premiered on HBO in March 2016. He won an AACTA Award (Australian Academy Award) for Best Directing for a Documentary, and a Walkley Award (Australian Pulitzer) for the film. The film was nominated for an Emmy Award in 2017.
Guttentag created and executive produced the NBC series Crime & Punishment, which ran 2002–2004. The show, a reality television spin-off of the Law & Order franchise, followed District Attorneys in San Diego County, California.
His novel Boulevard, was published by Pegasus Books/W. W. Norton in 2011, and the French edition was published by Éditions Gallimard (2013), where it was a finalist for the Grand Prix de Littérature Policière. He also co-wrote Masters of Disaster: The Ten Commandments of Damage Control, which was published in December 2012 by Palgrave Macmillan. He has also written nonfiction pieces, including for The Wall Street Journal and the Los Angeles Times.
Gutentag also directed Soundtrack for a Revolution, a film about music and the Civil Rights Movement. The film features performances by John Legend, Joss Stone, The Roots, Blind Boys of Alabama, Richie Havens, Mary Mary, Anthony Hamilton and Wyclef Jean. Soundtrack for a Revolution had its international premiere at the 2009 Cannes Film Festival, and its US premiere at the Tribeca Film festival. The film was released theatrically by Area 23a, and later aired on PBS. Guttentag was nominated for WGA and Producers Guild Awards for the film, which also won awards at US and international film festivals, and was short-listed for an Academy Award.
Guttentag's film, Knife Fight, which he directed and also wrote (with political consultant Chris Lehane), stars Rob Lowe, Jamie Chung, Julie Bowen, Carrie-Anne Moss, Eric McCormack, Jennifer Morrison, and Saffron Burrows. The film is about a Democratic political consultant and was released by IFC in January 2013. The film premiered at the 2012 Tribeca Film Festival, and also had special screenings at the 2012 Democratic National Convention and the John F. Kennedy School of Government.
Guttentag has directed commercials and other work for a number of Silicon Valley companies, including Google, Yahoo!, and MasterClass.
Guttentag has shown his films and given lectures at many US and international universities, including: Yale, Harvard, the University of California, Berkeley; the University of Pennsylvania; US; Peking University; Fudan University; Kyoto University; the Hong Kong Academy of Performing Arts; the Freie Universität Berlin. Other screedings include The Academy of Motion Picture Arts and Sciences; The Council on Foreign Relations; the Paley Center for Media; and the Brooklyn Academy of Music.Knife Fight (2013)
Soundtrack for a Revolution (2009)
Crime & Punishment (2002)
Twin Towers (2003)
The Cocaine War: Lost in Bolivia (1992)
Assassinated: the Last Days of Kennedy and King (1998)
You Don't Have to Die (1988)