5. "Sleep's Dark and Silent Gate"
Browne's wife, Phyllis, took her own life while he was in the midst of recording The Pretender, the album that became his most epic early accomplishment. The entire disc plays out like an elegy -- certainly for his spouse but also for the innocence and optimism spawned in the '60s and ambushed by the '70s. This song directly addresses the tragedy of suicide with musings on mortality, promise, and purpose.
4. "Before the Deluge"
In a very real sense, this song was a metaphor about a coming catastrophe, a description of dread that was so compelling, it could very well have changed life forever. Some saw it as Browne's farewell to a relationship, while others imagined something even more profound: the end of youth, the end of idealism, the end of hope for a better tomorrow. It still stands as one of Browne's darkest and most despairing testimonials.
See also: Five Rock 'n' Roll Plane Crashes