Likewise, we had jazz in the house all through my childhood, but the first thing I bought and took serious notice of was Nefertiti- the opening of Madness is still like the face of a parent to me- the first thing I recognized in jazz. After that it was Filles de Kilimanjaro, Four & More, plus Weather Report, Art Blakey. Out of my dad's old record collection I dug out a Norman Grantz Jazz at the Phil record and some Charlie Parker, and KOB. Apart from Blakey, it took me several years to come around on 50's bop where you could actually hear the drums. For that, Blue Seven off Saxophone Colossus was the entry track.My entry point into jazz was not bop. I only became a bop fan because I knew it was good and I liked it so I listened to it until I loved it. But at first it was not an easy listen for me. My first records that I really loved were Bill Evans Live at the Village Vanguard and Coltrane's Ballads, although my first jazz record was a Love Supreme, which I always loved. I still really love ballads and brushes like nothing else. Now I would say Milestones is my favorite Miles record or at least up there. I think that for really serious jazzers bop often tends to be an entry point, and I hear stories of guys who have 10,000 bop records. They hear it and it does something for them. At least that is what I have found. As we've said many a times, jazz is so unique anyone's entry point it going to diverge from the next person.
I wish I had your introduction to Coltrane- the first thing I bought was Om. It took me a couple of years to get My Favorite Things after that one.