Use LPR (Linux Print System), do not use CUPS. Many have complained that CUPS does not work with VMware but I don't have first hand knowledge of this.
If your printer isn't supported under LPR, make sure that you have the latest rhs-printfilters. If still no luck, then try using the LPRNG printing system, it has many more drivers available and is compatible with the LPR print system.
If your printer is working in Linux and it's not a "Winprinter" (see below), then you're ready to move on to the next step.
In VMware, go to: "Settings-Configuration Editor-Parallel Ports-LPT1"
Type = Device
Path = /dev/lpo (usually the default)
Check "Start Connected"
Click on "Install" then save and exit. You can also click on "Help" for more options.
("Bidirectional" is faster but can only be used with path = /dev/parport0, and only if your kernel supports this option. At this time I understand the 2.4.x kernel does not.)
First, go into "My Computer-Properties-Device Manager-Ports" and make sure that you have an LPT1 Port installed. If not, install one from "Control Panel-Add New Hardware" and select "Printer Port" from the list.
Next, install your specific printer driver as you would normally do in Windows and then try to print something.
"Winprinters" will not work in VMware, for example my Lexmark Z52 is considered a winprinter as it requires drivers as well as extra software provided by the manufacturer to function.
I have also setup an Epson Stylus 600 color printer and an ancient HP Deskjet 400, both of which are not winprinters and print like great from VMware, I can even use the Epson Maintenance utility to clean and calibrate the heads as well as detect ink levels.
As a side note, Lexmark does supply printer software for Linux that works beautifully and is identical to the software for Windows. CUPS also provides drivers for the Z52, however I haven't been able to get the Z52 to print in VMware. : (