None of these songs are really obscure, so let's get serious.
The Way it Used to Be. It's the best DT song that no one talks about.
The guitar is like what would happen if The Edge, Tom Scholz, and Jimmy Page's guitar styles got together and had a child (please just nod and move on). The drums and bass are some of the most musical stuff MP and JM have ever done. They're never literally melodic, but they feel like it. The keyboards are almost all background, but the tone is some of the most lush stuff DS ever played.
James LaBrie wrote the lyrics to this one. Unlike most DT lyrics, which are philosophical, optimistic, or outwardly confrontational, this song is very nostalgic. It's the only inkling I've seen from DT in any context wondering if they made the right life choices.
Take me back so I can see
the way it used to be
JLB doesn't sing it in a depressive way, which makes it even better. It captures that wistfulness we all feel and indulge in.
Listen if you can.