Yes, you can have two keys generate the same address.
There are 2^160 possible addresses, and 2^256 possible private keys, so each address corresponds to roughly 2^(256-160)=2^96 private keys. Any of these will generate the same address and thus be able to spend the money owned by that address. Since 2^160 is so large, however, it would take a near-eternity to find any collisions.
Whether two private keys can generate the same public key is another question. I think the answer is yes, but I am not sure on that. The public key in uncompressed form consists of two 256-bit numbers, which are X and Y coordinates on an elliptic curve. However, the compressed form is just the X coordinate plus a bit, from which you can calculate the whole public key. This means the space is (at most) 2^257. Unless there is a one-to-one mapping due to the mathematical properties of the cryptography used, each compressed public key corresponds to roughly 0.5 private keys (with the same distribution you'd get from picking a random number from 1 to 2^257, 2^256 times), so some private keys will collide, while others will not.
Actually finding any pair of different private keys that generate the same public key or address would be quite difficult. Either it would involve a huge amount of computation and/or luck, or it would be due to finding a serious vulnerability in the algorithm(s) used.