Jim, I have come to think that when someone says something is pretentious, they don't understand it. They don't "get" so it's pretentious. The word has entered the cellar of meaningless words.
I grew tired of rock fairly early. I did always know Dylan was a genius and liked other singer-songwriter music. Then I had a friend and he introduced me to jazz. It took a few listens, and then I was hooked as usual I dived full of treading and listening to what I could afford. It is truly America's classical music. I grew up in the same town as John Coltrane. It was a bit of a local story when he died.
As for listening, I wouldn't start with Coltrane's major works. He's a giant but is challenging in his great albums. He made a few much more accessible albums, one with Ellington and another with singer named Johnny Hartman, which is perhaps the most romantic album ever made.
I went through a period when I was obsessed with Art Pepper. A bit part of it is he wrote the best book about addiction there is. I guess De Quincy is one but I haven't read it. The memoir is called "Straight Life: The Story of Art Pepper." Truthfully, he's not a major figure. He didn't change jazz the way Louie and Parker and Coltrane did, but he is one of the best alto sax guys ever. Here is a link to a short album. The story is he was hung in his house doing dope and his manager arranged for Miles Davis's rhythm section to wake him up. They did this little album in one day and it's a classic. Some simple and accessible and he could always let you know where his life was in solo.
I honestly think his memoir is a giant book and not just for the drugs stuff.
I have tons more suggestions and anecdotes and such. Jazz has been with me through everything. It is intimate the way other musical forms aren't. I know you're an Angelina fan. It's the jazz in her voice that makes her different than anyone. She has said Billie Holiday was where she started.
I almost forgot the Modern Jazz Quartet. So simple and pretty with still creating rhythms like no one else.