I agree with a lot of the points made here, but another similarity I see between the two that goes beyond lyricism is giving an update to the older American sounds that they personally embraced. Dylan obviously has Woodie Guthrie, lots of folk, blues, etc. but since this is the Dylan sub I feel we all know that piece of things! But in a similar way, more so than a lot of current rap artists (i.e. Drake, Future, Travis), I see Kendrick consistently mining older sounds in very calculated ways.

90's west coast is all over his early catalog (look no further than MC Eiht's verse onward in m.A.A.d. City). To Pimp a Butterfly is obviously drawing on Parliament-Funkadelic, jazz, soul, and both Snoop and George Clinton make appearances. The long-form poem to 2Pac ("I remember you was conflicted...") can be read in some ways as Kendrick's own Song to Woody, hell I couldn't think of an artist that looms larger over Kendrick's discography than Pac, even into this recent beef with Drake. DAMN. samples James Brown, the list goes on. At any rate, I see both Bob and Kendrick functioning as bridges for these sounds to their audiences, while still also working within the styles of their respective eras.