Half-life 2 gave me a black screen on Maverick until I upgraded to latest nVidia from ubuntu-x-swat x-updates PPA, and wine1.3 from ubuntu wine team PPA. Before the update from wine 1.2 (from the regular Maverick repos) I also installed directx9 with winetricks (from the repos also.) Presumably those files are still in my wine setup.
UPDATE 200802120955 PST: On my system (Ubuntu gutsy, wine-0.9.47) this seems to be working. I will leave this page up for posterity. --drink
Since about 0.9.13 or so Wine has been capable of running Steam and its attendant games, which includes items like Half-Life 2. However, steam backups don't seem to want to work properly.