Apple played such a large part in bringing about the changes that have made music retailing what it is today that it becomes almost impossible to comprehend the scale of its miss on streaming music. Having been late to the party Apple went for a quick fix by paying through the nose for Beats and its existing music streaming service. In the transition it managed to achieve two almost unthinkable things - it delivered a truly bad product and it alienated some of its biggest fans.
Apple Music is something of a train wreck.
That's overstating the case of course - with 13 million subscribers Apple has the second biggest on-demand music streaming service in the world. It's hardly something that you'd describe as a failure by any other company's measure.
For Apple though it has been a worrying sign of fallibility that draws some interesting parallels.
Rewind just a few years and Apple basically owned the music business. Sales of music through iTunes were the biggest and fastest growing methods of consuming music. Steve Jobs had managed to force the music industry to bend to his will - first in setting a fixed price for music and second by ensuring that tracks were available individually and not forced on the consumer as an album purchase.
Like Microsoft with the internet two decades ago, Apple completely missed the rise of the streaming music business. As Spotify grew its subscriber numbers Apple failed to spot the coming juggernaut that was coming to derail its gravy train. Even Microsoft reacted more swiftly and Apple was eventually the last big name to get into the game.
When it did so it managed to so badly manage the Apple Music app, service and desktop integration, that users were dissuaded from signing up in their millions. The free trial to subscription conversion rate is low - and slowing apparently - and the bad blood that came from destroying customer's carefully curated music collections still colours Apple Music today.
So the news that Apple is aiming for a do-over of the software and service is critical. Nothing the company has done has been this badly received since the Apple Newton. Putting it right - and demonstrating that it can be trusted to manage customers music and streaming - would indicate that all is still right in the Apple world.
With an estimated one billion iOS users out there - a captive audience for Apple - it seems barely believable that the service has only been able to convert such a small cohort of users. It seems highly unlikely to me that when Tim Cook dropped $3bn on Beats he would be expecting to have seen such a minimal return from the streaming service.
With streaming now generating more income than downloads, its a situation that Apple needs to turn around. Quickly.