Lipton began his career as a graphic artist and won an award for his illustration of a version of the Haggadah, the Passover seder liturgical text.

During the 1920s, he associated with Chicago writers Edgar Lee Masters, Sherwood Anderson, Harriet Monroe, Ben Hecht, and Carl Sandburg.

[1] His other novels include Brother, The Laugh Is Bitter and In Secret Battle, as well as a poetry book, Rainbow at Midnight.

In the episode "Swan Song" on the show Gilmore Girls, Rory is showing Jess her copy of The Holy Barbarians by Lipton, and says that he is "the father of the guy that does those Actors Studio interviews on TV", to which Jess responds "It's weird that a beatniky guy would have a conservative son like that."

He next married Betty Weinberg, a teacher; their son was Inside the Actors Studio host James Lipton.