Do remastered albums ever sound better than the originals?

I own multiple CD and/or digital copies of a lot of albums. The original CD, the remaster, sometimes a deluxe edition or an anniversary box on top of that. They all sit in the same library in Roon, and every time I hit play I'm implicitly choosing one of them (Roon sets one of the copies as "primary"). This bugged me because I didn't know which one would objectively sound better (I clearly have problems). So I decided to stop guessing and measure it to help me: which version of each album is the most dynamic? The short answer is that the original pressing usually wins, and the exceptions are super interesting, so I thought I'd write it up. (This post is about CD/digital remasters—I know vinyl is a whole different ballgame.) How I measured My CD collection is ripped losslessly (mostly FLAC files), a little over 2,100 albums across 603 artists. For every track I calculated crest-factor dynamic range, the same DR measurement the Dynamic Range Database uses. Take the difference between…