Bruce Springsteen has covered hundreds–many hundreds–of songs in concert, so we count ourselves fortunate if even a single performance of a song was captured on tape or video.

So how lucky are we to have not just one but five versions of Roy Orbison’s all-time great on video in spectacular quality?

Pretty darn lucky–especially because it took all five times before Bruce could make it all the way through the song without incident.

Orbison’s original rendition of “Oh, Pretty Woman” is one of the greatest recordings in rock and roll. From the instantly recognizable riff to Roy’s inimitable growl and soaring vocals, “Oh, Pretty Woman” topped the charts for three weeks in 1964 and finished in the #4 slot for the year.

Bruce first covered it in 1987, when he performed it with the original artist himself right after Bruce inducted Orbison into the Rock and Roll Hall of Fame. Bruce spent much of the star-studded performance star-struck–watch below as Bruce gets a kick out of Roy’s “Mercy!” at around the 1:45 mark and completely forgets the lyrics a minute later.

Bruce kept it together a lot better the next time he took a crack at it, only eight months later at the filming for Orbison’s classic concert film Black & White Night. But in this performance, Bruce stays firmly on backing vocals, stepping to the fore for an extended guitar duet with Roy during the second half of the song.

It took almost twelve more years before we’d get to hear Bruce play “Oh, Pretty Woman” with the E Street Band, but that moment finally came when a fan requested it at Bruce’s concert in Munich on July 2, 2009. It’s a loose, fun performance, even if (or especially because) at times it seemed like Bruce might not be able to hold the song together for much longer–the ending gets particularly hairy. By the end of the song, Bruce is clearly exhilarated from having made it all the way through:

Two months later, that moment must have still been on Bruce’s mind, because during his taping of a special multi-part appearance on Spectacle: Elvis Costello With… Bruce decided in the moment that he and Elvis should give it a go. Did they make it all the way through? See for yourself:

But practice makes perfect: just a few weeks later, Bruce decided to give “Oh, Pretty Woman” a try again. This time, though, he was ready for it–he had John Fogerty enlisted as a partner and they’d rehearsed beforehand. So when the moment came on-stage at the Rock and Roll Hall of Fame 25th Anniversary Concert, Bruce, John, and the E Street Band rose to the occasion.

Here’s their (finally) perfect cover of Roy Orbison’s “Oh, Pretty Woman” from October 29, 2009:

Oh, Pretty Woman
First performed: January 21, 1987 (New York City, NY)
Last performed: August 1, 2015 (Asbury Park, NJ)

 

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