The Don Cherry stuff is pretty great music by any definition. Strong melodies, and great playing, swinging. The NY Contemporary Five is a lot shaggier, but it is nice example of a real open quarter swing and solid free bop. I like Don Moore's bass playing and he has nice connection with JC Moses.I love those Don Cherry's and I think they're a great into to Free Jazz (whatever that is - I'm uncomfortable using that term). That early Shepp stuff not so much. 4 For Trane is a much better starting point IMO. I really love his later stuff too which shows how beautifully an "out" player can apply his language to standard jazz material.
Don Cherry is a lot more of a central figure than he is often positioned as. He did so much as a side man to so many of the early great players that you can really get a good picture of the music just by tracing his movement through it. His own albums are fantastic as pointed out above.