If we're thinking logically as in who had the most left to give and never got to contribute to the musical world the full extent of what they were capable of I'd have to say either Jeff Buckley or Big L.
Buckley was obviously a seriously talented musician as well as being able to produce stellar emotionally driven performances in both his lyrics and musicianship He in my eyes could easily have went on to have a long and illustrious career the likes enjoyed by Cohen and Waits. Perhaps even more successful as I think on a purely talent based level, he was superior.
Big L was one of the best rhymers in a packed NY scene at the time of his rise to prominence. Revered on the underground circuit; as a freestyler and a battle rapper, L had just signed with Jay-Z's Rockafella Records when he was murdered. With financial backing, better production and marketing he could easily have went on to become the most popular MC of all time or had he stayed with his street based style could have released several 'classic' albums
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