Bob Dylan- Blonde on Blonde (1966) & Blood on the Tracks (1975)

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My two personal favorites by the most timeless lyricist of every generation.

Blonde on Blonde was considered the first true significant double LP in rock and roll music, and is always at least in the top 10 in most/all major music critics top records of all time lists. B.O.B. has the Highway 61 Revisited-esque blues sound, but more refined and with much more surreal lyrics. Its also the last record Dylan recorded before his motorcycle accident that significantly changed his singing/songwriting forever.

Blood on the Tracks was Dylan's first studio album since Blonde on Blonde that received mass praise from critics and fans. To this day he claims his lyrics were never autobiographical, but the heart wrenching songs on this album that revolve around heartache, anger, and loneliness seem to tell all too well a tale of loves lost that we can all relate to, whether Bob was speaking from personal anguish or not.