4. No Rest for the Wicked- Season 3, Episode 16
Deans deal is finally up.. In just a few hours his soul will be sent to Hell for eternity. There is only one thing that can save him. He must kill Lilith before 12:00 or the Hell Hounds will rip him to shreds. Throughout season 3, the brothers did everything they could to stop Dean from being sent to Hell. Now time is up. The only person that can save Dean is someone he hates the most, Ruby. She has the weapon that can kill Lilith. It's ironic that Dean must finally trust Ruby. Of course he punches her in the face first. Everything about this episode is heart breaking. Sam and Bobby force Dean to let them help even if they are caught in the crossfire. Lilith possesses a little girl and kills her family one by one when they disobey her. Sam and Dean sing Bon Jovi's "Wanted Dead or Alive" while driving to their deaths. It's a beautiful scene even if they can't sing. Of course the most tear jerking scene is the final 5 minutes of the episode. Lilith secretly takes over Ruby and traps both brothers. There she releases the Hell Hounds who brutally rip Dean to shreds while Sam has to look on. It's the biggest cliffhanger on the show because one of its two protagonists is sent to Hell.