Guttentag won an Oscar for Best Documentary with his HBO film You Don't Have to Die,[1] telling the story of one boy's battle against cancer.

Nanking featured Woody Harrelson, Mariel Hemingway, Rosalind Chao, Stephen Dorff, and Jürgen Prochnow.

[5] Guttentag directed, co-wrote and co-produced the dramatic feature Rule Breakers, which will be theatrically released by Angel Studios in Spring 2025.

Guttentag partnered with Richard Linklater on That Animal Rescue Show, on which they were executive producers and directors.

The show, a non-fiction spin-off of the Law & Order franchise, followed District Attorneys in San Diego County, California.

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, with Democratic political consultant and presidential advisor Chris Lehane, which was published in December 2012 by Palgrave Macmillan.

The film was produced and distributed internationally by Wild Bunch and released theatrically in the U.S. by Area 23a, and later aired on PBS.

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, David Harbour, Eric McCormack, Jennifer Morrison, Michelle Krusiec, and Saffron Burrows.

Guttentag has directed commercials and other work and been an advisor for a number of Silicon Valley companies, including Google, Yahoo!, Mattermost and MasterClass.