Mark Knopfler’s Sailing to Philadelphia Two Decades Later.

Rediscover the “lost art” of making an album by revisiting this Mark Knopfler classic from 2000.

Sailing to Philadelphia by Mark Knopfler is available on Amazon.

One of things that live streaming and downloadable songs by demand has tended to obscure is just how beautiful a well crafted album of original music once could be. It’s not just the cover art, the vinyl records, the shiny, rainbow-hued CDs, the liner notes, the acknowledgements, or the properly credited names of the guest vocalists and backup musicians – although it is also all those things. It’s how all the pieces precisely fit, how one song follows another; how the pace, tone, and rhythms ebb and flow and rise and fall and crescendo into showers of sparks, only to fade away back to deafening darkness. It is very much like a sonic-and-lights fireworks display, as you experienced such spectacles as a child, not a jaded adult fading into old age and decaying memory.

And that’s just when the album is released, at the time. What’s equally amazing is how you can take the album off the shelf – years if not decades later – to replay the songs to discover how much your listening world and sensibilities have changed. 

Sailing to Philadelphia was released in 2000, when Mark Knopfler was approaching the age of 51 (he was born in August 1949, a Leo). Now, he’s almost 70 and has several additional albums out there, including Down the Road Wherever (2018). At times like this, I enjoy replaying older albums to see how much has changed. Who changed more, I wonder: Mark or me?

The songwriting talents of Mark are as strong as ever, but what makes Sailing to Philadelphia so memorable, in retrospect, is the array of guest vocalists who joined him on the album, and in the way that the songs capture something about the year 2000 – the start of a new millennium, after all – that makes all of his songs historical, and not just the ones he intended. 

The most famous duet here is arguable with James Taylor on “Sailing to Philadelphia,” a creative imagining of the story of Charles Mason and Jeremiah Dixon, British surveyors who mapped the southern border of Pennsylvania that became in time a diving line between free and slave states. While this is a great song, when I first listened to this album it was “The Last Laugh,” which featured Van Morrison as guest vocalist, that caught my attention.

Now, in 2021, I have come to love “Silvertown Blues,” and the vocals of Glenn Tilbrook and Chris Difford, in a song about a gentrifying docklands district of London that has by now been completely transformed by 20 years of urban redevelopment. So, the song is a time capsule, and it sounds like a Western country song, but set in a frontier-like section of London. How quintessential Knopfler is that!

The other thing I really appreciate now, that I probably missed in 2000, is the pedal and lap steel playing of Paul Franklin on multiple tracks, including “Wanderlust” and “The Sands of Nevada,” both of which I appreciate more now than I did earlier. 

All the songs here are historic, now. In 2000, some were explicitly set in the past, but others were meant to be contemporary. Listen now to “Do America,” “Speedway at Nazareth,” and “Junkie Doll,” and you are hearing ghosts of the past. Nazareth Speedway, in Pennsylvania, has now closed, its race track shuttered and empty. And who takes a “777” to L.A. anymore? And the drugs taken by mark’s “junkie doll” are probably hard to find anymore, what with all the prescription opiates and Chinese-made fentanyl available for purchase on the Internet. 

I loved most of these songs when I first listened, but now my ears have changed. They ring a bit more now at night when they did back then, but the quality of my listening has changed as I approach my own experience with middle age. Mark’s songs on Sailing to Philadelphia aren’t necessarily about getting older, or wiser, or more skeptical of the world’s glittering array of pleasures, but they do reveal a shifting mental landscape of a male musician who had seen decades of life already, with decades more to go. Hard to rate that on Amazon, so this WordPress review will have to suffice.

Published by Sempervirens117

I am a content writer and founder of, an eco consultancy based in Woodside, California that assists Silicon Valley companies in developing greener products and promoting sustainable Earth solutions on social media. I offer team training sessions year-round in Northern California.

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