I have to agree with what I’ve read here.
Watch the Ken Burns Series!!!!
Some many great stories are told in this series. The first episode is about the historical roots of jazz and may seem a bit removed, but hang in there. I don’t know your age and who you’ve grown up with, but I have a huge appreciation for Louis Armstrong because of this series, as well as more enjoyment of many artists because of his perspective.
Also, Clint Eastwood’s movie “Bird” helped get me into Charlie Bird.
I was in HS 2971-74, an era where “jazz” was associated with the stuff mothers did not approve - thus entered the era of the “stage band” in high school. We barely played any jazz, and the only ones keeping jazz alive were big band stars like Woody Herman, Buddy Rich and Maynard Ferguson, who were wise enough to add some rock tunes to keep us youngsters listening.
My advice: Find a “way in” that you like and continue to expand your horizons. Mine was through Buddy and Maynard and their high power big bands, learning what I liked, and slowly branching out.
Find some standard 40’s big band tunes you like. This is an easy “pop” way in toward appreciating swing time.
Like Latin? Head that direction - lots and lots to choose from in that venue.
About all that soloing...it will grow on you. Really. Not all of it, but some. I still can’t stand - i.e. understand - “A Love Supreme” by Coltrane, but I’ll listen to most of Miles all day long.
(This next section is pure jazz sacrilege, but too bad...)
A few more thoughts about that soloing stuff. I like to divide soloing (improv) into two camps (and of course this is way too simplistic, but bear with me). There are solos/soloists that “play around with the tune” and those who just “play the changes”.
If you’re having difficulty with the likes of Bird and Coltrane et al, it might be because they tend to leave the tune behind and focus entirely on the chord changes. Other soloists like Miles, Stan Getz and Wynton Marcellis for example solo “around the tune” while they improv over the changes. Many find this much more accessible. It is NOT better or worse, but if your having trouble with one, try the other camp. A final note (shhh...this one is really, really sacrilegious)... you ARE allowed to fast forward through the solo (I’m checking over my shoulder for the jazz police as I write this).
Other approaches:
Find a tune you like, and listen to several versions of it. Nutville (Nuttville), Autumn Leaves, I Can’t Get Started are a few that come to mind.
Try WATCHING some jazz - that approach can make it more appealing.
In this day and age of streaming music “learning to like jazz” is a lot easier and infinitely cheaper than 50 years ago. Skip through some “Essentials” of some artists
Here are some tunes/artists I find to be “more approachable”:
Enjoy the journey...
Miles Davis - So What, Freddie Freeloader, Walkin’,
Cannonball Adderley - Autumn Leaves (weird intro)
Stan Getz - Girl from Ipanema, Four Brothers
Sonny Rollins - St. Thomas, The Eternal Triangle,
Chet Baker - Autumn Leaves
Dave Brubeck - Gone With the Wind,
Bill Evans - Waltz for Debbie, Autumn Leaves,
Horace Silver - Nutville, Cape Verdean Blues, Song for My Father
Big Band Sounds: pick a few and see what gets your foot tapping.
40’s
Benny Goodman - Stompin’ At the Savoy,
Artie Shaw - Begin the Beguine
50’s - 60’s
Stan Kenton - The Peanut Vender,
Dizzy Gillespie - Manteca, Night In Tunisia
Count Basie - April in Paris, One O’clock Jump, Shiny Stockings
70’s
Woody Herman - My Favorite Things, Somewhere,
Maynard Ferguson - MF Horn 1 @ 2
Buddy Rich - Big Swing Face album, West Side Story Suite