Where exactly did the slang phrase "digging it" come from

I'm a young native english speaker raised in Canada. At school me and most of my friends tend to use the phrase "Im really digging this", as to mean i'm really enjoying a specific thing or activity. Where exactly did this come from?

I use it all the time in this context, but when I think about digging ( like digging a hole, or digging yourself into a mess) I can't really make sense of it in this context.

Ex:

"You play that new game that just came out?"

"Yeah bro, im really digging it!"

From EtymOnline:

In 19c. U.S. student slang it meant "study hard, give much time to study" (1827); the 20c. slang sense of "understand" is recorded by 1934 in African-American vernacular. Both probably are based on the notion of "excavate." A slightly varied sense of "appreciate" emerged by 1939.

So there were a few intermediate steps between "digging a hole" and "digging a game". The direct connection is unintuitive, but only because of the way the latter developed.