I have to come down strongly as a no on this one. A poor recording is a poor recording. The system can't put anything there that isn't there. It is my belief that the measure of analog is analog. That is you don't really see the value of analog so much from comparing it to digital recordings as in comparing good analog recordings to poor or indifferent ones. I think this is what really makes you appreciate the artistry of producers and engineers in getting sound onto an analog medium. I recently had a general upgrade of my system that particularly improved the analog side, and it is quite the experience to listen to a record you know of old find it sounding better than it ever sounded before. But when played through the same equipment you will find that there are recordings that just fill the room and there are others that lay there like a lump. One thing I've been doing as I revisit my LP collection is listening to the English folk music I love, and I still love the music but by and large they really weren't that well recorded. On the other hand, while it may just be an effect of what's in my record library, what I've been particularly impressed with are record from the Warner/Elektra/Asylum menage, For example, Paradise and Lunch by Ry Cooder, and Swordfishtrombones by Tom Waits. Actually, one of my more unusual analog appreciation moments was listening to an old Alan Sherman record and being struck by how good it sounded.
On the digital side, I once tried something I think of as the DAC/CD Death Match, when you take an early digital recording you know to be pretty dire and run it through a good DAC to see if it can be redeemed. My match was a Denafrips Ares II vs. the extraordinarily harsh MCA Broadway Gold digitization of the original cast album of Porgy and Bess circa 1992. I'm afraid the CD won that one.