- Summertime: improv with A minor pentatonic (yeah, every guitar player knows)
- Maiden Voyage: with dorian mode
- Cantaloupe Island: dorian and mixolydian
- Autumn Leaves: major ii-V-I
- Sunny: minor ii-v-i
This set (and in this order) pretty much mirrors what we did at SJW (add your choice for a rhythm change tune: Oleo or Anthropology!)
And if you check out this list from my other fav Jamie Holroyd, you would find similar tunes:
- Summertime: same as above
- So What: dorian
- Tune Up: This is actually my go-to tune for practicing ii-V-I changes
Yes, you really should learn to play Summertime: the melody, improv and comping. Matt Warnock taught several commonly seen jazz voicing for Summertime here.
Speaking of comping and voicing, I do have a counter example. Another online teacher put up this video and was promoted by GuitarPlayer: 3 Easy Jazz Songs - For People Who Don't Play Jazz! Don't get me wrong: I really appreciated his effort in getting more people to play jazz. However, jazz players simply don't play that! First of all, his video taught the chords of the songs (without the melody) so I'd say it's a bit misleading. Second, it's one thing to know and learn to play those chords (Drop-2 and Drop-3 chords in Berklee's terminology) In a real jazz jam situation you won't play those chords like that though. When you jam with a piano and/or bass, you won't play the low notes on your guitar since it would clash with them. Guitar players should stick with those "upper voicing" when comping.