My experience has been that not all USB-parallel cables are created equal. I wanted to use my fine old HP Laserjet 4 Plus with my macbook pro, and my first cable (startech.com) never worked. I tried the gimp-print driver and the foomatic driver, the standard usb backend, and usbtb -- at best I could get the lights on my printer to blink. My /var/log/system.log would record various usb errors, and nothing would print.
I bought another cable today (IOGEAR GUC1284B) and it worked on the first try with the standard usb backend and the CUPS-Gutenprint driver. In particular, when I added a printer from the "Print and Fax" panel, my Mac detected the USB device correctly as a HP printer; with the other cable, it found a "IEEE 1284 cable" or whatever instead, and left it up to me to choose a driver.
My guess is that my first cable was doing an inadequate job of returning signals from the printer. Presumably there is a small chip at the fat end of these parallel-usb cables, powered by the usb port, that does the work of converting between a serial port (usb) and a parallel port (printer) -- these send their data using quite different mechanisms, so the cable actually has to do some "computing" to work. Some of these chips may well take shortcuts that don't always work.