2. Bob Dylan, Modern Times (2006)
More than anything else, Modern Times proved age is not necessarily related to the quality of one’s musical output. From the opening notes of the rollicking “Thunder on the Mountain” to the eight-minute epic “Ain’t Talkin’”, Bob Dylan demonstrated that, nearing the age of seventy, he possessed as much energy and desire for experimentation as artists decades younger than him did. Borrowing from sources as diverse as 19th century folk and 20th-century pop (“When the Deal Goes Down” directly quotes a song by Bing Crosby), Modern Times showed North America as viewed through the eyes of one of its greatest songwriters, a land where the past, while constantly in the shadow of the present, was never far behind.