Harry the Hipster was a character from Sam and Friends, Jim Henson's 1955-1961 daily puppet show. He was a black sock-puppet type of Muppet with white shades. He was a lover of jazz who always spoke in hip slang. He is best known for his appearance in the Sam and Friends episode "Visual Thinking".
Harry was one of the first Muppets designed and built by Jim Henson.
Harry with Sam in The Muppets: A Celebration of 30 Years
In the 1940s, jazz musician Harry Gibson was billed as "Harry the Hipster." Gibson also did some childrens records in the early 1950's, such as "Jack and the Beanstalk, a Fairy Tale For Hip Kids," possibly inspiring Henson, who was in the age group to have been a "hip kid" around that time.