Do you check the oil on or off the stand 1995 softail?

The oil level should be checked with the bike standing upright (not leaning on the jiffy stand) and at normal operating temperature. And to be perfectly accurate, both tires should be level with each other.

However, once you've established the correct oil level using the above method, you can lean the bike over on the jiffy stand, let it cool off for an hour of so and then read the level again in that position.

Whatever that reading is on the dipstick, use it as your reference to check the oil when the bike is cold and leaning on the jiffy stand.