10 “Beautiful Loser” by Bob Seger

Bob Seger is one of the most featured artists on , and he has several hits, but the show uses his songs especially well. “Beautiful Loser” is one example of this. In season 4, episode 17, “It’s a Terrible Life”, Same and Dean are put into an alternate universe where they’re not brothers and have normal lives.

Dean is a hotshot VP at his company, and as he gets in his car to start the day, “Beautiful Loser” starts to play. It’s the perfect song because Dean is living the lyrics as someone who wants everything, but hasn’t realized that eventually something is going to give.

9 “Wanted Dead or Alive” by Bon Jovi

is most known for the emotional scenes between the brothers, second only to the numerous times they die. Season 3 starts with Dean preparing to go to Hell in one year because he sold his soul to bring Sam back to life after his first death on the show. Sam and Dean get into an argument because Sam wants to save Dean, and after an awkward moment, “Wanted Dead or Alive” ironically comes on the radio.

Dean starts singing along, and eventually, Sam joins in. While it’s sardonic, the two brothers singing along to this song together is a touching moment of reprieve after an emotionally charged season.

8 “The Gambler” by Kenny Rogers

In a show filled with classic dad music, Kenny Rogers had to make an appearance.

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