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So, the tail lights on the '55 four hundred work when the lights are on, but they don't work when the brakes are pressed. Where could the problem be?

The brake light switch is mounted to the frame under the battery tray and the round vent tube. If the car is still stock, 3 wires are in a sort of plug which pushes down onto the switch prongs. Make sure that assy is on tight and the contacts have a good connection. The pink wire is the power in and on 55s comes from the body feed fuse in the fuse block under the dash. The dark green wire is for the brake lights and the light green wire is the power to the torsion level on/off switch under the dash and then on to the level switch.

First check the fuse but unless there has been a problem with the wiring chances are it is OK. If the car has sat a long time or used silicone fluid, the 3 terminal brake switches are known failure items and expensive to replace with another original. There is an aftermarket 3 terminal hydraulic switch that someone can give a part number for. Those require a terminal change and have been reported as not having a long life either. There are some kits to replace the 3 prong switch with an ordinary and inexpensive 2 prong switch plus a relay to work the TL system. Another mod is to replace the hydraulic switch with mechanical. Either of those options have a better longevity If it turns out you need a new switch.