The words 
hep and 
hip are of uncertain origin, with numerous competing theories being proposed. In the early days of jazz, musicians were using the 
hep variant to describe anybody who was "in the know" about an emerging culture, mostly black, which revolved around jazz. They and their fans were known as 
hepcats. By the late 1930s, with the rise of
swing, 
hip rose in popularity among jazz musicians, to replace 
hep. Clarinetist 
Artie Shaw described singer 
Bing Crosby as "the first hip white person born in the United States."
[1]
In 1939, the word 
hepster was used by 
Cab Calloway in the title of his 
Hepster's Dictionary, which defines 
hep cat as "a guy who knows all the answers, understands jive". In 1944, pianist 
Harry Gibson modified this to 
hipster[2] in his short glossary "For Characters Who Don't Dig Jive Talk," published in 1944 with the album 
Boogie Woogie In Blue, featuring the self-titled hit "Handsome Harry the Hipster".
[3] The entry for 
hipsters defined them as "characters who like hot jazz."
Hipsters were more interested in bebop and "hot" jazz than they were in swing, which by the late 1940s was becoming old-fashioned and watered down by "
squares" like 
Lawrence Welk, 
Guy Lombardo and Robert Coates. 
In the 1940s, white youth began to frequent African-American communities for their music and dance. These first youths diverged from the mainstream due to their new philosophies of racial diversity and their exploratory sexual nature and drug habits.