Friedman was born in Seattle, and attended Garfield High School. Enlisting in the US Army Air Corps in World War II, he achieved the rank of 2nd Lieutenant. As bombardier of B-24 and then B-17 aircraft, Friedman flew 36 missions over Belgium, France, Holland and Germany in the 861st Bomb Squadron, 493rd Bomb Group, 3rd Bomb Division, 8th Air Force. After his tour in the European Theater of Operations, he gained his commission and trained to become a pilot. He was released from the Air Corps at the convenience of the Army on 17 October 1945, after the war's end. For his air service in operations over Normandy, Northern France, the Rhineland, and the Ardennes, he was decorated with the Air Medal, 1 silver cluster (5 earnings).

After the war, Friedman took a degree in English Literature from the University of Washington. He then moved to New York City, where he began shooting hundreds of photos in his spare time. Many of the prints appeared in prominent newspapers, including a widely-circulated photo showing Friedman's wife Jean and his small son Nick expressing surprise at a seemingly broken water fountain suddenly springing to life. Another photo of Henry Cabot Lodge, Jr., former U.S. Ambassador to the United Nations, and his wife on a bench in Central Park, appeared on the front page of the New York Herald Tribune.

After an incident where Friedman, attempting a nature shot while perched precariously on a log over a stream, fell and doused himself and his camera, he focused his efforts primarily on writing. He wrote four books, Those Magnificent Kennedy Women, Ronald Reagan: His Life Story in Pictures, The Kennedy Family Scrapbook, and True Quotes (the last under the pseudonym of "Ike Macgillicuddy"). Friedman was also photo editor on Robert MacNeil's acclaimed book, The Way We Were: 1963, The Year Kennedy Was Shot.

Friedman was the author of numerous freelance articles in such publications as The New York Times, New York, Esquire, National Lampoon and the Village Voice. He conceived of a layout for a 1981 Esquire article entitled "Got the Picture?", which went on to win a national design award. It consisted of a two-page spread containing empty rectangles where photos might logically appear, under which captions written by Friedman described famous events in modern history that were so prominent in the public mind that many swore they had seen the photographs, though none existed. Among them: Kruschev using his shoe as a gavel on the dais during a U.N. speech, and Babe Ruth pointing to center field in the 1932 World Series prior to hitting a home run there.

A lifelong movie buff, Friedman appeared as an extra in 1982 in Still Of The Night, starring Roy Scheider and Meryl Streep. Friedman vowed to pursue his writing career "until they find me dead at the keyboard." True to his word, his end came just a few feet away from his computer, in his sleep, on July 14, 2006. The screen contained a poem Friedman was composing. He was buried, as per his wishes, with a cup of coffee and a New York Times in his coffin. His epitaph: "Fifty Years on the Writer's Rock Pile."