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Somewhere I have a Reichsmark from I think 1937, definitely my favourite... it's actually shiny too. I haven't looked at the dates on every coin I have but I think they go back to the mid 19th century, so not all that far.
The € has been around here for a decade now (I don't know exactly how long, but that's what it feels like), but I still have some Deutsche Mark lying around in the house. The oldest one I found was a 2 Pfennig coin from 1959.