Death is not only a concept that 'Supernatural' is literally based upon, it is also a character on it (one that strangely loves fast food). This just goes to show how the TV series is affiliated with its characters dying, although it has taken it a bit too far. During the course of 12 seasons both the Winchesters have died a couple of times, and although the first times were more emotional, the fans now do not believe death is permanent for the Winchesters. In a recent interview, Jensen Ackles stated as to why Dean Winchester witnessed death such a strange amount of times (although to be fair any amount above one counts as odd).

Why 110 times?

Every fan has to admit that the first time Dean died, which was due to the end of the demon deal to save Sam, was devastating, but it didn't last long.

He came back to life after the angel Castiel raised him from perdition, as part of God's plan. Another memorable time would be when he was banished to Purgatory for standing too close to the spell that vanished the Leviathans. However, the largest number of deaths ever recorded within such short period of time in the history of television, to actually make people laugh, was when Sam Winchester was stuck on a loop by the Trickster.

The Trickster was trying to teach Sam a lesson about how he could never save his brother from dying, and that he would actually be better off focusing on learning how to live without him.

The end of the episode became downright depressing, even though the rest of it featured some very comical moments between the Winchester brothers and Dean dying. Sounds odd to say it, but that has been noted as one of the funniest episodes of the entire series.

And that is the reason why Dean's death count is much higher than the death count of Sam Winchester (without that particular episode they would have died an equal amount of times).

What about Sam Winchester?

The writers actually intended to make another episode for Sam, but Jared Padalecki refused due to advice that was given to him by Andy Richter from New York Minute, regarding the rule of not dying more than six times. Although this is not in his contract or something Jared is particularly concerned about.

It affected the writers' ideas of putting Dean in that situation, instead of having Sam deal with it. Furthermore, Jensen Ackleshas never felt nervous about the idea of his character having these temporary deaths, which also gave the show runners more space to explore those kinds of episodes. Dean Winchester not only has beaten death just like Sam Winchester has, he has also killed it (to save little Sammy of course).