I got both games on this CD to work this weekend. My steps:
For Sam and Max: I tried everything else, but eventually got the game to work using the updated EXE (
http://www.samandmax.net/index.php?section=hittheroad&page=techhelp). Copy the BUILD\SAMNMAX directory to \SAMNMAX on a hard disk. If you don't want to waste HDD space and have a CD burner, you may be able to build a CD. But it's less than 500MB, so it's not really worth it, IMO.
I haven't worked out how to turn off the 'smoothed' graphics, which I don't really like.
For Day Of The Tentacle: step one, install VDMSound (
http://ntvdm.cjb.net). Step two, copy the BUILD\DOTT directory to your hard disk. Step three, edit DOTT.BAT so that the 'tentacle' line reads:
tentacle s220/7/8 g m
This tells DOTT to look for a SoundBlaster for playing wave audio at I/O port 220, IRQ 7 and to use 8 buffers, to play music through General MIDI, and to use the mouse. If you've edited VDMSound's VDMS.INI to change the emulated IRQ (you may find that sound is choppy on the default IRQ 7, or that some games don't support it - I use IRQ 5), replace the 7 with the IRQ you're using.
Step 4, right-click on DOTT.BAT and choose Run with VDMS.
Step 5, get out of my house! (sorry, couldn't resist).