Well, let's see:
Three-a-day practices in the August heat in college getting ready for season. That was tough every year in college. It never got easy. Lots of puking, light headedness, and just praying for it all to end. But the worst was as soon as you got the pads off in the locker room, you knew you'd be out there again in 3 hours, and it'd be hotter.
Then there was the suicide test sprint. You had to run 20 consecutive 40-yard dashes, with no more than 30 seconds rest between sprints. Your time was averaged, and ranked into your position on scout team as a redshirt, or if you actually got to dress. Not the only factor, but it was a big one. So you pushed and puked your way through it. Because they ran this right as the first thing you did when you showed up to camp, you were not ready for it like you would have been 5 games into the season. Even though you trained for it.
Bodybuilding diet in the last week with the carb and water cut. That's a long week filled with longing, suffering, dizziness, temptation, self-doubt.
But by far the hardest thing I've ever done physically was freestyle wrestling in college. I remember going the distance against the number one ranked guy in another state. He beat me 6 to 4. It was the longest, hardest match of my life. I had cut too much weight to make 209 in too short a time. I was gassed after a minute (my fourth match that day), and though I thought I had a shot going in, towards the end, I was hanging on for dear life trying not to get mercy'd. It's why I very much respect what MMA fighters can do. My lungs were burning so badly it hurt to breathe. I remember laying down for 30 minutes after the bout and not wanting to move.
The most painful thing, was when I branded the inside of my palm with a large piece of iron that I thought had cooled off. Having some beers with buddies near the bonfire. The metal poker we used to keep the fire hot usually sat to the side. I thought I had only left it in the fire for a few seconds, and picked it up. I was wrong. It was more like 30 minutes. Complete 3rd degree burns through the palm of my hand. It's amazing how sensitive the palm of your hand is. The pain was off the charts. People who choose self-immolation as a suicide are crazy. If I was a in a burning building with no chance of rescue, I'd jump.