7. Bobby
Actor: Jim Beaver
"“Ya Idjits.” -Bobby"
Bobby wasn’t supposed to be a longtime character. His popularity kept him around longer. Even after he died, Bobby returned multiple times throughout the series. Everyone loved him for his sass, smarts, and knowledge of killing monsters. However, his love for the Winchester boys was his most redeeming quality. He turned those boys into adults with love and kick in the butt when they needed it.
6. Lucifer
Actors: Mark Pellegrino, Misha Collins, Jared Padalecki
"“You really thought you could double-cross me? Me?! You know, I invented the double cross, like, literally.” -Lucifer"
Sure, Lucifer was an awful person who wanted humans extinguished. Yes, he actively tried to bring forth the apocalypse. But he was entertaining while he did it. He always had a one-liner and a snappy response.
Lucifer was more than just quips. He redefined everything that the Devil is supposed to be. Of course, he was evil, but he gave you a reason to understand his motive. Listening to his, “… do you know my crime? I loved God too much.” speech made sense. Especially after you see how God was ready to exterminate humanity.
5. Crowley
Actor: Mark Sheppard
"“You’re right. I am a monster and I’ve done bad. I’ve done things you can’t even imagine. Horrible, evil, messy things. And I’ve loved every damn minute! So, thank you, Sam. For reminding me who I really am.” -Crowley"
Crowley was another villain who wanted to be better. The former crossroad demon and King of Hell always managed to be helpful. He had enhanced strength, but that wasn’t his greatest ability. It was his charisma. Throughout the series, Crowley sweet-talked his way out of trouble. Sadly, his mouth got him into trouble as well. Either way, he was always.