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Dave McNaughton's When I Paint My Masterpiece playlist

As May 2021 marked Bob Dylan’s 80th birthday, we went to our resident ‘guru of groove’, Dave McNaughton, for one of his legendary playlists. Here is how Dave met Bobby D.

Growing up in Napier in a household of classical musicians, no commercial radio was ever played and television strictly policed. By the time I got to high school, pop and rock music was starting to seep in. Elton John, Paul McCartney, and Don Mclean were top of my great songwriters’ list. 

My friend Paul had older brothers and sisters at university, and he had hundreds of their records at his place. He decided to take over my musical education starting with Highway 61 revisited at full blast on his parent’s stereo. You remember them, I’m sure. A console with a turntable, big amplifier, and huge stereo speakers in each corner of the room. The pop pretenders were swept aside with the opening organ chords of Like a Rolling Stone, and the world has never been the same again.

Dylan, the man, has never stopped creating and challenging himself. So many musicians and artists live off their old hits or stay stuck in their heyday. Not Bob. He keeps on moving forward. Like a rolling stone! While he is a famous icon, you rarely see him in the gossip pages — he remains a mystery. Where does he live? How many kids does he have? Is he or is he not married? I don’t know. To me, that shows he has a healthy sense of private versus public awareness. I like that about a person. His music can be sung by crooners, like the Bubble, or rough country riders, like Willie or The Band, and stand up well to any interpretation you care to give them. 

When I Paint My Masterpiece is an unreleased gem later recorded by The Band with slightly tweaked lyrics on their album Cahoots. It’s a measure of Bob’s greatness that three of his best songs, this one, I Shall Be Released, and Blind Willie McTell, were never included on his studio albums — and he gave away two of these songs to The Band. I love the feel of When I Paint My Masterpiece. There’s a sense of wistful regret and nostalgia in the lyrics combined with minimal instrumentation and unrehearsed vocals — it’s a killer track.

I’ve tried to represent Bob’s output over the last six decades. Apologies for the absence of any live tracks, no jazz standards, or anything from his religious phase. Maybe next time in When I Paint My Masterpiece No. 2. In the meantime, happy birthday, Bob, and happy listening to you!

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