Engine Timing Issue has me pulling my hair

[viscoelastic]

Serious timing issue. Just bought a 66 mustang w/Inline 6. It idled rough when I looked at it, but was not worried since it has been sitting in a garage since 1990.

What I have done, Drained the fuel, new carb, replaced; plug wires, spark plugs (gapped them), ignition coil, cap, rotor and swapped out points for electronic trigger. After this I had difficulty even starting it.

Here is where it is strange. I rolled the engine to TDC on #1, the timing mark on the crank was on the mark. I pulled the distributor cap and the rotor was at #5 not #1. I twisted the distributor so the rotor was on 1 and it wont start, rotated the distributor and when it started and ran rough, when I checked it again it was on #5. It wont run or start with the rotor on 1 at TDC. Put a timing light on it and its about 60 degrees out and runs?

Why would I have to retard the distributor one entire cylinder out for it to run, In fact, I don’t think it should run at all.

Thanks in advance

 

[WORTH]

You have to be a tdc on the compression stroke. pull #1 plug, put your finger in the plug hole, tap the key until it blows your finger out, then slowly rotate til your at tdc. Then after she starts, put the timing light on it.

 

[tos]

You have to be a tdc on the compression stroke. pull #1 plug, put your finger in the plug hole, tap the key until it blows your finger out, then slowly rotate til your at tdc. Then after she starts, put the timing light on it.

I'm going to add to Worths comments - After you get that pressure from the number one spark plug hole and rotate your engine to line up your timing marks then check to see if your rotor is lining up to number 1 position. If its way off then its likely someone had the distributor out at one time and got it off a few teeth when they re-installed it.
You could put your timing light on the number 5 wire and see if your marks are showing up better on that position to verify that it is off as well.

I would also verify you have your wires in the correct positions on the distributor (make sure you know which direction your rotor is supposed to turn and make sure your firing order is matching).