Shubert I don’t think jazz will ever come close to the popularity it once had. Great performances live, as you have pointed out, will help but the younger generation has to be at these shows to begin with.
As far as jazz being main stream to the masses, which will never happen, here is a man that since I started posting here I have never seen mentioned and he pulled it off with this song:
https://www.youtube.com/watch?v=4IyXo9jL7VcFrom Wiki:
Leaving military service, he worked in New York City before returning to Chicago where he signed a contract with
Vee Jay Records. His first album for Vee Jay,
Exodus to Jazz, included his own jazz arrangement of
Ernest Gold’s theme from the movie
Exodus. A shortened version of this track, which featured his masterful playing in the upper register of the tenor saxophone, was heavily played on radio and became the first jazz record ever to be certified gold.
The single climbed into the US
Billboard Hot 100 and reached No. 16 in the U.S.
R&B chart. Some jazz critics, however, regarded commercial success as a sign that a jazz artist had sold out and Harris soon stopped playing "Exodus" in concert.
[3] He moved to
Columbia Records in 1964 and then to
Atlantic Records the following year where he re-established himself. In 1965, Atlantic released
The In Sound, a
bop album that won back many of his detractors.
I have the Exodus to Jazz disc and quite a few other Eddie Harris recordings including this gem at Montreux with Less McCann on piano:
https://www.youtube.com/watch?v=_UrjQSVbIkk&list=PLm7ogPYlDbGyVNmwz2txcpKuDKk4opeVH