The way I see it - if your long run puts more stress on you than the fitness you have got to productively absorb it, it will not be productive. You cannot develop the fitness by running just once a week to be able to absorb your long run. So you need to "earn" it in a sense by running adequate mileage more or less evenly spread throughout the week.
So let's say you have been running 3 miles a day 6 days a week, and that is the most you have ever run in your life. If you are not some odd edge case, you will not be able to productively handle anything much longer than 6 miles - though you definitely can go much further, and maybe can even finish the marathon before they close the course. However, if you gradually up your daily mileage to 10, then you would likely benefit from 18-20 mile long runs because you are more fit.
The pitfall I see many runners fall into is they see that they CAN run long, so they do, but they do not ask themselves - is this long of a run actually improving my fitness? I have fallen into that trap myself more than once. In 2003, for example, my fitness got to the point where I could race a full marathon in under 2:30 and not be sore after I finished. Interestingly, I got there with the long runs of only 20 miles. I thought - now I should be able to handle a 26 mile long run in 2:55 with the last 10 miles at 6:00 pace. Not so, it gradually wore me down and I lost the fitness.
What I learned in 34 years of running is that top effort in training often does not produce top results in racing. Rather, a relatively moderate but very consistent effort with occasional pushes to max out the engine very much in moderation is what gives you your best race.