Aaron and Brent both highlight music from singer-songwriters: a Virginia native who got his start performing for inmates at maximum-security prisons and a California born musician who amassed a following in the early 1990s by playing at venues in Manhattan's East Village. With songs that explore the tension between light and dark in life, Aaron looks at three songs from Matt Maeson. Known by many for his reconstructed cover of Leonard Cohen’s “Hallelujah”, Brent dives into the career of the late Jeff Buckley by showcasing three songs from his catalogue.

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