GYPSY TALES

Chapter 417

Charley Boorman

14 Aug 2026 · 3h 16m

With Charley Boorman

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Charley Boorman sits down with Jase to tell the real story behind Long Way Round, the trip with Ewan McGregor that changed the motorcycle adventure genre forever. From how the idea came together over dinner in London, to the Dakar Rally training that got him ready, to riding the Road of Bones across Siberia to Magadan, Charley walks through the trip that shaped his life. They get into what four months on the road with Ewan actually taught him, how the Sky One deal came together, the Long Way Down and Long Way Up follow-ups, riding Australia end to end, 53 miles of hard enduro at the Isle of Man with David Knight, and what makes Jett Lawrence and Marc Marquez operate on a different level than the rest of us. Whether you've watched every Long Way series or you're finding Charley for the first time, this is the interview that goes deeper than the shows ever could.

Photos 1

Charley Boorman — Gypsy Tales episode photo

Chapters 40

  1. 0:00Intro
  2. 1:54Welcome Charley Boorman to Gypsy Tales
  3. 2:26Jase on the Subscribe Discovery
  4. 4:57Meeting Charley at the Isle of Man TT
  5. 10:16The David Jeffries Story
  6. 14:40Cardo Systems Ad
  7. 22:01Riding Australia End to End
  8. 25:49Living in Queensland with Jason Connery's Mother
  9. 34:57Racing the Dakar Rally
  10. 37:07The Race to Dakar Documentary
  11. 40:04What It Takes to Make the Dakar
  12. 50:54Coming Back to Dakar
  13. 52:13Jumping Into Long Way Down
  14. 54:37The Real Story Behind Long Way Round
  15. 1:03:47Getting the Sky One Deal
  16. 1:07:06Motosport Ad
  17. 1:13:54Collecting Dream Motorcycles
  18. 1:24:05Why Ewan Wanted to Do the Trip
  19. 1:30:04Riding Into Russia
  20. 1:38:38Jase's Scottish Roots
  21. 1:39:33Through Mongolia
  22. 1:41:12The Road of Bones to Magadan
  23. 1:45:51Magadan to Anchorage
  24. 1:51:05Long Way Round
  25. 1:58:19How Long Way Round Inspired So Many
  26. 2:04:27Fist Handwear Ad
  27. 2:07:51The Making of Long Way Down
  28. 2:12:58Africa in All Its Vibrance
  29. 2:19:04The Dangers of Border Crossings
  30. 2:32:29Charley's Dream Australian Ride
  31. 2:36:56Ducati's Desert X
  32. 2:37:38The Bike Charley Bought Himself
  33. 2:42:4153 Miles of Hard Enduro at the Isle of Man with David Knight
  34. 2:47:04What Makes Elite Riders Different
  35. 2:47:40Sota Fuel Ad
  36. 2:48:28Why Jett Lawrence Is So Good
  37. 2:51:43How Soccer Players Handle Injuries vs MotoGP
  38. 3:00:58Charley's Bucket List Rides
  39. 3:07:38The European Bucket List Tour
  40. 3:14:02Closing

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