Should, but doesn't. The versions match, too - that is, debug 3.6.5, regular 3.6.5. On the retail, it starts the music, hitches, dumps FS2 almost into a window - that is I see my desktop and a 1024x768 black box in the upper-left corner indicating it's considering windowed mode, and then eventually it coughs out the CTD.
I think what's actually happening is it's generating the CTD and it exits ... less than cleanly.
Debug, worked fine first try, then I switched back to the regular EXE and it's been well-behaved ever since.
I've got no idea why it's doing that...