My top a few most favorite song lyric writers/singers

Isaac Brock
This man expertly captures the ecstasy, agony, and angst of being. He doesn't use a lot of complex or obscure words in his songs, but he is a master of lyrical construction, flipping simple phrases back on themselves to succinctly explain an idea. The spaciness of Modest Mouse's musical composition greatly enhances the gravity of musings, and his loud, angry, soft, reflective, fucking pissed delivery makes sure you'll remember what he has to say.

"The universe is shaped exactly like the earth, if you go straight long enough you'll end up where you were."

Tom Waits
Master past, present, and future. The slurred, carnival barker voice coupled with lyrics consisting of reminiscing about a man with two faces or a piano player with no body is eerie enough in its own right. Add in the ability to croon like Frank Sinatra with a gizzard full of gravel and his breadth of emotion is boundless.

"And I must be insane/to go skating on our name/and by tracing it twice/I fell through the ice/of Alice"

Craig Finn
Injects a huge amount of humanity into the situation surrounding junkies, drunks, pimps, and other "low lifes". His drunken delivery is suitably intoxicating, and the stories, which normally involve everyday people with bad judgement, are excellent at expressing the fragility of any given situation and the potential fall lurking behind any decision.

Conor Oberst
He can handle any subject thrown at him dealing with nearly any existential issue with sublime grace. He will sometimes make reference to obscure events to enrich his material, and allow the listener the opportunity to do some research to enhance their understanding of the music.

Neil Fucking Fallon
Pure fun, with a razor sharp wit. References tons of historical events, literature, and mythology. Delivers it all with a terrible roar and energy.