I had a DM that always did his best to keep the party intact. One of us might roll low on something we were trying to do, and he would do his best to make sure you came out even or at least alive.
Well, I had a dwarf fighter who had gotten separated from the party. He was taking a shortcut through the mountains to a dwarf stronghold to meet back up with his fellows.
His mode of transportation was taking an elaborate “box chute” system. A cable car that took you from the mountain peak to the dwarf stronghold at the base of the mountains.
During my journey, my DM had me roll to give me updates on how my character’s trip was going. I proceeded to go on a string of rolling single digits and natural 1’s…. And my DM really bent over backwards to ensure my survival. My dwarf ended up falling out of the chute. I did several “climb and hang on” checks…only for the dwarf to fall…roll survival checks to make ensuing crawl checks on the mountainside while my dwarf did his best to stay alive. At the end of it…He froze to death in his plate armor. And the chute had continued on with no driver…so that it crashed into the stronghold, killing several NPCs.
That, unfortunately, became my style of play. My ensuing D&D career consisted of futile characters with unique deaths.