As far as his own music goes, special emphasis goes to "Grace", "Lover, You Should've Come Over", "Morning Theft", "Vancouver", and "Jewel Box".
Jimmy Page thought Buckley was playing in alternate tunings (something Page is fairly familiar with). When he saw him perform, and realized that he was playing it all in standard tuning, he became one of Buckley's biggest supporters.
Covered Up - His rendition of Leonard Cohen's "Hallelujah" has arguably become more widely used, more popular and better known than the original.
Funny Moments - Most of the monologues on the "Live At Sin-e" Legacy Edition. It's like the man was walking jukebox.
Harsher in Hindsight - The title track from Grace, in which Buckley sings "And I feel them drown my name", is eerie considering how he died. The final track on Grace - "Dream Brother" - also ends with the line "Asleep in the sand with the ocean washing over."
Tear Jerker: "Hallelujah" is a Musical one but the real one comes from the tragedy that both Jeff and his father never lived to fulfill their true potential as musicians.