Where using pry (0.10.0) with pry-coolline (0.2.4) and cooline (0.4.4), you need to push the up arrow button twice (instead of once) to get the last entered expression, like there was always an extra empty entry at the command history.
This is happening to me using ruby 2.1.2p95 (2014-05-08 revision 45877) [x86_64-linux].