Wow! Cool jazz, hot topic indeed! My story's a little different.
I'm an easterner. It was Shorty Rogers who first transported me out west. This was in the day before his Big Band Express. I was midway through high school, suffering from an overdose of Glenn Miller and looking for some fresh music to play with a small group, and I happened to see an advertisement for a couple Shorty Rogers arrangements in Down Beat, "Morpo" and "Pirouette." I bought them and then bought the recording, a 45RPM album titled Shorty Rogers and His Giants. Yep. still have the charts, still have the recording.
In an effort to learn more about Shorty's arranging techniques, I reversed-engineered the parts and made a concert-pitch score. So that started me on a track of arranging.
The album itself sent me looking for more recordings by Shorty and his sidemen on this recording, among them Jimmy Giuffre, Milt Bernhart, Johnny Graas, Hampton Hawes, and Shelley Manne. Actually, I was greatly disappointed at first because I was unable to find anything by the exquisite alto player listed as Art Salt. It took me a few weeks to figure out that the performer whose recordings I should be looking for was actually Art Pepper. So all this was my introduction to jazz. I wouldn't know about Miles Davis or Charlie Parker or any of the cats performing closer to home for months, maybe years to come.