He studied art at Straubenmuller Textile High School in Manhattan and fine arts at Cooper Union in New York, graduating in 1949.

In the 1960s Charlip created a unique form of choreography, which he calls "air mail dances". He sends a set of drawings to a dance company, and the dancers order the positions and create transitions and context.

He has performed with John Cage, he was a founder member of the Merce Cunningham Dance Company for which he also designed sets and costumes, he directed plays for the Judson Poet's Theater, he co-founded the Paper Bag Players, he served as head of the Children's Theater and Literature Department at Sarah Lawrence College. He won two Village Voice Obie Awards, three New York Times Best Illustrated Book of the Year citations, and was awarded a six-month residency in Kyoto from the Japan/U.S. Commission on the Arts. He has written and/or illustrated 29 children's books and currently lives in San Francisco, California, USA.