For me, getting into Dylan took just one thing:
"The Freewheelin' Bob Dylan."
The voice, the intimacy (he's right in yer ear...), the imagery ( "lit a cigarette on a parking meter..."), the fingers pointed, the logic offered, the ill-logic offered, the yearning expressed, the humor, the cool-as-shit stereo mix, the cool-as-shit mono mix...
Okay, I'm just gushing now...
Start here and you'll be hooked for life. I sure-as-hell know I am.