Dean Winchester is one of the most beloved characters in Supernatural, but throughout the shows 15 seasons, there have been alternate versions of Dean introduced. Dean Winchester famously died more than 100 times in Supernatural, but audiences rarely got to see a different version of the character. After going through so many traumatic and terrifying experiences, its not a surprise that the Dean audiences saw die in the Supernatural series finale was very different from the Dean introduced in the series pilot.