“Couldn’t hold a note”: The singer Bob Dylan said was better than Roy Orbison

Posted On June 9, 2025June 9, 2025

Every rock and roll singer has those standards that they set for themselves before they even sing a note. Some people might always throw caution to the wind and sing however they feel on the day of a show, but the real skill comes from someone knuckling down and delivering the kind of performance that the true crooners of rock and roll could be proud of. And while everyone Bob Dylan came up with looked to Roy Orbison as a major inspiration, Dylan knew there were far different avenues for people to go down than his amazing voice.

Then again, it’s hard to find much to dislike about what Orbison brought to the table. Compared to the raw power of Elvis Presley or the shock factor of Little Richard, his crooning voice on ‘(Oh) Pretty Woman’ sent chills down the spine of everyone who heard them, leading to everyone from Bruce Springsteen to John Lennon wanting to get the same vibrato out of their voice when they sang their classics.

But it was clear that Dylan would go that route when he sang. Most of his songs could get rambly in the early days, but that conversational quality in his voice always set him apart from his contemporaries. He was preaching as much as he was performing half the time, and if that meant not having the same moody voice of Orbison, he was more than okay with that.

Granted, Dylan was no one-trick pony when it came to the type of music he liked. He had no problem talking about how R&B lit a fire under him when he started listening to it or even praising the biggest names in punk for making rock and roll sound important again, but bluegrass has always been the cousin to Dylan’s brand of folk music. Whereas Dylan used his guitar as a weapon, bluegrass did have a bit more musicality to it, and The Osborne Brothers taught him everything he needed to know about vocals.

Bands like The Beatles and Crosby, Stills, and Nash might be the gold standard for what many people think of when it comes to perfect vocalists, but Dylan knew that the bluegrass collective was unparalleled in their field. It’s one thing to be able to play those instruments with such precision, but to go from that to singing in perfect harmony with each other was enough to put Orbison to shame.

According to Dylan, what the band could do with notes was miles ahead of anything that Orbison could have done on the song ‘Ruby Are You Mad’, saying, “The Osborne Brothers are a high-powered bluegrass group. Maybe the most high. Roy Orbison couldn’t hold a note as long as this guy who is singing high tenor. The Osborne Brothers sing extremely exquisite harmony lines.” But the most impressive part about the song isn’t even the vocal harmonies; it’s about the arrangement.

Since the recording is completely barebones, there’s hardly any drums for anyone to focus on where the beat is. All these players only have to rely on their ears and their internal sense of timing to get them to the other side of the song, but when listening to them lock in with each other, you would have sworn that everything came like it was second nature to them whenever they sang.’

Although Orbison was a fantastic singer and clearly blew everyone in the Traveling Wilburys out of the water when he played, there was something much more refined going on with the Osborne Brothers. This was the kind of music made by people who lived and breathed every note they sang, and that passion is impossible to fake.

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