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‘Sailing To Philadelphia’: Mark Knopfler Crosses The Mason-Dixon Line

The former Dire Straits frontman hit a particularly rich seam with his second LP in his own name.

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Mark Knopfler 'Sailing To Philadelphia' artwork - Courtesy: UMG
Mark Knopfler 'Sailing To Philadelphia' artwork - Courtesy: UMG

The solo album catalog of Mark Knopfler contains nothing but exquisitely crafted songs that uniquely tie together the roots music of British and American culture. But most Knopfler fans would agree that the former Dire Straits frontman hit a particularly rich seam when he released his second LP in his own name, Sailing To Philadelphia, on September 26, 2000.

Since then, Mark’s rate of productivity has travelled in the opposite direction from that of most long-standing artists. In the following 15 years, he made six more solo records, in addition to numerous other productions, guest appearances and his ever-extensive touring.

But in 2000, Sailing To Philadelphia arrived after a gap of four years from Knopfler’s official solo debut (not counting film soundtracks), Golden Heart. There was, in the interim, the small matters of an extensive tour behind that first album and scores for Metroland and Wag The Dog. 

The Beatles - Now And Then
The Beatles - Now And Then
The Beatles - Now And Then
Mark Knopfler - What It Is (Parkinson, 22.09.2000)

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A literary influence

Ever open to inspiration from the arts, and especially from literature, he was moved to create the new songs after reading Thomas Pynchon’s novel Mason & Dixon, based on the lives of Charles Mason and Jeremiah Dixon. They were the English surveyors who created the Mason-Dixon Line, the symbolic boundary between free and slave states before the American Civil War. It still denotes the divide between the Northern and Southern United States.

Knopfler’s enterprising casting for the title song had him singing the role of Dixon (“I am a Geordie boy…it was my fate from birth, to make my mark upon the earth”) while James Taylor played “Charlie” Mason (“It seems that I was born to chart the evening sky…they’d cut me out for baking bread, but I had other dreams instead”).

“James had asked if I’d produce him,” revealed Knopfler at the time. “We had a couple of chats and it occurred to me that he would be really ideal to play this part, if you like. With James’ folk background I thought he could play Charlie Mason really well.”

The album was a Top 5 hit all over Europe, reaching No.1 in Germany, Italy and elsewhere and going gold in the U.K., U.S., Australia and beyond, and platinum in several other countries. Among the other dozen songs on it was a cameo by another famous artist that Mark greatly admired, Van Morrison, on “The Last Laugh.”

‘A thrill to hear Van’

“Van has been so much a part of my life, since I was a kid in university,” said Mark of Morrison’s appearance. “It’s a thrill to hear him singing a song you’ve written, because of what Van’s music has meant to me over the years.”

Listen to uDiscover Music’s Mark Knopfler Best Of playlist.

Other highlights included “Silvertown Blues” (featuring Knopfler’s old friends Glenn Tilbrook and Chris Difford from Squeeze), “Junkie Doll,” the single “What It Is” and two tracks containing particularly fine Knopfler guitar performances, “Speedway At Nazareth” and “Baloney Again.” Read about more of his finest guitar work in this dedicated story.

Buy or stream Sailing To Philadelphia.



  1. Sharat Walter Rao

    September 28, 2016 at 7:45 pm

    Sharat suffered a severe traumatic brain injury at 21.(18 years ago).
    He was a lead guitarist and has clung to Mark KNOPFLER’s music right
    through his sad and lonely life struggling with the loss of his past life.
    He has Aphasia and has asked me to say :
    Mark Knopfler fantastic . Thank you
    very much.
    Sharat Walter Rao

  2. salah

    January 23, 2017 at 10:41 pm

    mark knopfler is my good idol

  3. Art

    January 23, 2018 at 11:11 pm

    The Last Laugh with Van Morrison is a personal favourite, would love Mark & Van to record an album together.

  4. Mary Walke

    January 24, 2018 at 9:04 am

    I have always been a Dire Straits fan since they began and after have bought Mark’s albams. I find his voice and his music very relaxing. And I listen every day. The last one I obtained was Tracker. And I love it.

  5. Rui Alves

    September 26, 2018 at 9:42 pm

    I run a little café called PASTELARIA ELÓIVO since 2000 in Campolide , Lisboa , Portugal and the only one CD playing in that day was SAILING TO PHILADELPHIA by MARK KNOPFLER . I love that album .

  6. Steve (but not Naive)

    September 26, 2019 at 9:30 pm

    A beautiful and wonderful album from a man who has given us the lion’s share of beautiful and wonderful music for so many years.

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The Beatles Red and Blue Boxsets
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