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Musician Robbie Robertson at the Windsor Arms Hotel in Toronto.Moe Doiron/The Globe and Mail

"You got any more unanswerable questions?"

That's what Robbie Robertson asks me, but the interview is actually going fine. We're talking about dying young and living tragically. Robertson, 70, all in black, is fit and pleasant – plenty more waltzes for him. Others weren't so lucky. "Some get out alive," he says, as we talk in a suite at the swanky Windsor Arms Hotel in Toronto. "And some don't."

Robertson, famously and formerly the Band's songwriting guitarist, has co-authored Legends, Icons & Rebels: Music That Changed the World, a coffee-table book written with a special eye toward young listeners. It's a richly presented survey of melodious originators, from Louis Jordan to Bob Dylan.

What struck me about Robertson's roster of greats is the number of troubled souls and/or premature deaths on the list: Johnny Cash, Buddy Holly, Ray Charles, Elvis Presley, Marvin Gaye, James Brown, Patsy Cline, Sam Cooke, Otis Redding, Billie Holiday and Hank Williams.

Asked about them (and others not in the book, including Etta James, Charlie Parker, Robert Johnson and Janis Joplin), Robertson ponders the romanticizing of bothered artists. Do we apply an extra level of admiration to a drug-addled performer? Did their demons contribute to the profoundness of their work? Do we get a high from their lows?

"I saw Ray Charles at Massey Hall," Robertson says of a Toronto show in the 1960s. "I thought, looking at him, that it wasn't an entertainer doing his thing. I thought, 'Wow, look at him, he's a heroin addict.' To my fantasy imagination, at a very young age, I thought the addiction must be a part of it. He didn't talk to the audience. He didn't seem to care."

To Robertson's mind at the time, the drugs and the music added up to something heavier. As he got older and witnessed the needles and the damage done, his romantic notions were dispelled. "I learned pretty soon, after seeing Ray, that the drugs didn't have much to do with it. I didn't like what anyone did any better or worse because they had drug or alcohol issues."

But is it possible that a particularly soulful artist is served by their worried mind? Is a van Gogh or a Van Halen tapping into something? "It's hard to say," says Robertson, whose bandmate Richard Manuel was a bottle-a-day drinker who committed suicide at age 42. "They may have been better without the addiction. It's an unanswerable question."

Fair enough.

Yet, thinking of Charles, do we not consider his plight, as we listen to him singing blue? In the book, Robertson tells an anecdote about Charles and the Massey show, where he had to leave the concert after hearing Drown in My Own Tears. "It was so powerful, so moving, that I couldn't take it."

Perhaps more moving than an artist with a jones is one that died young. What would Redding or Holly have achieved? It's hard to listen to Dock of the Bay without attaching the extra dose of heartbreak that comes with someone being lost in his prime.

Robertson isn't as romantic about the connection between addictions and artistry. "There's just as many people who did terrific and didn't have a life of tragedy," says the man who wrote The Shape I'm In for the troubled Manuel to sing. "It's just everyday life."

And everyday death. In the end, Robertson finds the cases of Redding and Holly the saddest. "They," he says of the two icons who died in separate airplane crashes, at age 26 and 22 respectively, "didn't do anything wrong."

No question about that.