I had very weird problem with my old (but very reliable) LaserJet 1100A printer connected to parallel port. The problem was simple but fatal - everything went OK with success everywhere, but nothing happened on printer itself.

The solution was to change driver from CUPS based to Foomatic based. Tested on Ubuntu LTS 14.04.4/32bit

Steps to change the driver:

• select System tools - Printers in your Ubuntu menu
• choice your LaserJet 1100 printer (it should be detected and installed)
• choice Properties from context menu
• Click on Make and Model - Change...
• keep Select from a Printer database, and "HP (recommended)"
• click Forward
• on left side keep LaserJet 1100 selected (there is no need to switch into 1100A - the only difference is added/missing scanner device)
• on right side change selection from "hpcups" to "foomatic/ljet4"
• click Forward
• click "Print test page"

It should work now.

Connecting LaserJet 1100 via OEM USB --> LPT (FD25) converter

Even if you have no longer paraller port you can still use great LaserJet 1100 printer with OEM USB --> LPT (FD25) converter

• Follow above setup instructions with just one difference:
• Ensure that your device URI is now parallel:/dev/usb/lp0 (instead of parallel:/dev/lp0 for real parallel port). This tip comes from https://ubuntuforums.org/showthread.php?t=894223&page=11&p=10530838#post10530838

Diagnostics: please use lsusb to verify that you have same adapter:

lsusb
   ...
   Bus X Device Y: ID 067b:2305 Prolific Technology, Inc. PL2305 Parallel Port
   ...