Don't you think you're relying on having your characters roll natural 20s and one hundreds a bit too much?
Critical Fail Spot Check
Some people just get that lucky. Just like how some people are literally that UNlucky.
A roll of 100 is actually a bane for me. And so it comes up a LOT more often than I'd like. 1% is actually a very high chance in an RPG, statistics be damned.
they seemingly were rolling a lot
They don't tell us all the numbers rolled or how many rolls have been made in this comic. take a look at the fact that Luke hit that rock wall 5 times on low rolls, meaning that he likely rolled 20 times by that point alone, if not more.
I'm pretty sure on the boat before the bird, they said he had to roll a 99, not a 100...
...a 100 is more dramatic.