well I'm running HL 1.1.1.0 in WINE (free version, not non-free version of Cedega/Winex) and it's all okay... except the fonts are a little ugly, but it works
I can also cross-compile windows binaries in GNU/Linux btw
edit:
well AFAIK it doesn't "hang", and it actually crashed.
run WINE in the shell and when it "hangs", press alt+tab to switch to the terminal window and it will give you the information to say it crashed.