For me, I'd say the Korg KPR drum machines for my analog choice. Just for the snare drum alone (which will be familiar to anyone who owns Depeche Mode's first album...)
For digital, I'm going to make an unconventional choice in the Fricke-512B. This not-very-well-known 8-bit drum machine just sounds so amazingly crap that it's brilliant in a way. Reminds me of the Korg DDM-110, which was my first drum machine, but I think the Fricke is a bit more unique-sounding.
So what are yours? Answer in the comments!