2x08 “Crossroad Blues” // 11x15 “Beyond the Mat” Demon Deals
I was really surprised when I realized that Aleks Paunovic, who played the wrestler Gunnar Lawless in 11x15 “Beyond the Mat”, had been on Supernatural before. The show has used many actors multiple times in different roles, but him I definitely hadn’t remembered to have been on the show prior the S11 episode. :) Funnily enough, even though this is hardly intentional, the two episodes he appeared in connect pretty well with one another as both of these episodes are centered around demon deals and the aftermath of making them.
Back in S2 the episode heavily foreshadowed Dean selling his soul and going to Hell - dying in fact, like Aleks Paunovic’s character says about his former colleague here, “way too young”. In S11 we see that very experience come back into play when Dean tries to help Gunnar Lawless and tells him that he has been in his shoes, sold his soul too, was desperate too, but still believes that despite having made mistakes before, people can do the right thing.