Installed from origonal 1.2 CD. Install went fine however I forgot there was a video at the end of the install process that you can not skip and it runs so slow under crossover. Once however it had finished I applied the Windows 1.21 patch and loaded Kingpin up. On the first load you get the Interplay movie but this is a one off and the next time you load it is fine. As mentioned below there was no sound when I first started up so went in to Options and then changed the sound settings to Max Compatibility this kicked the sound in and I could change it back to performance.
Ran at 600x480 and 800x600 with no issues. Have not tried to play online but I know there is an anti cheat program called Monkey mod that is a separate exe file used to stop cheating and this needs to be loaded first and this is required for most servers.
Running Mac OSX 10.4.8 and Crossover 6.0 Beta 3