I don't think I've run into any "Live at the Village Vanguard" release for any jazz artist that was bad listening. John Coltrane is no exception. It's probably more difficult to find an album of his that sucks. But I would recommend any versions of "Favorite Things" as it's a good example of Coltrane taking a pop piece and converting it to "sheets of sound." Supposedly Miles Davis asked Trane one time why he did such long solos. Trane answered to the effect "Because I can't figure out how to stop the solo. I can't think how I should finish it." To which Miles replied "Take the horn out cha' mouth."

I'm not a big band enthusiast.. but likewise it's tough to find things bad by Duke Ellington. He's considered the greatest jazz composer. There's an "Ellington and Coltrane" album that's quite good.
And of course there's Miles Davis. The thing with Miles is that he spans many styles. When he first came on the scene he got to sit in with Dizzy Gillespie's group in Harlem. Dizzy played so fast Miles just couldn't keep up. It may be as a reaction to this that he adopted the emphasis on "using space." One of his quotes is "Don't play what's there. Play what's not there." The CDs Cookin', Relaxin' etc. from the 50s are among the best of his work of that period. Kind of Blue and other works of the 60s. Then he got into more avante garde or free form stuff like Bitches Brew, Pangea, even using a Whah whah peddle on the trumpet in the late 60's and early 70s. I especially like the album Water Babies.. all the tunes written by Wayne Shorter. In fact Wayne is a good listen. 60s classics like Speak No Evil will never go out of style. He and Joe Zawinul(who wrote Mercy Mercy Mercy which broke through to the top 40) founded Weather Report... fusion at its best.
My technique was sort of "spider web" and I recommend it. If you have an album you like a great deal, look at the personnel. Find albums by each of those and try to sample them. The various quintets and other groups of Miles Davis is a good place to start. Wayne Shorter, Herbie Hancock, Paul Chambers, Wynton Kelly, Bill Evans, Joe Zawinul.. I just never heard any bad albums by any of those guys.
Then when you find an album of one of the Miles "side men" that you like very much.. continue the process. Almost like a recursive algorithm. It just keeps fanning out.