My favorite Bobby scene ends up on that list for a lot of people. It's in All Hell Breaks Loose, part 2 when Dean and a revived Sam go to Bobby's and he takes Dean out into the junkyard to confront him about making a deal.
BOBBY What is it with you Winchesters, huh? You, your dad. You're both just itching to throw yourselfs down the pit.
DEAN That's my point. Dad brought me back, Bobby. I'm not even supposed to be here. At least this way, something good could come out of it, you know? It's like my life could mean something.
BOBBY What? And it didn't before?! Have you got that low of an opinion of yourself? Are you that screwed in the head?! (He grabs DEAN again)
DEAN I couldn't let him die, Bobby. I couldn't. He's my brother.
BOBBY How's your brother gonna feel when he knows your going to hell? How'd you feel when you knew your dad went for you?
DEAN You can't tell him. You can take a shot at me. Whatever you got to do, but please don't tell him.
BOBBY begins to cry, grabbing DEAN'S chin.
I wish that Dean might have absorbed that message a lot earlier. As it is, I'm not sure he buys it now.
I like their farewell hug at the end of Swan Song
Bobby and Dean always seemed to have an easy relationship. Sam and Bobby are close but it's a different kind of relationship. Here's their last exchange before Sam said yes to Lucifer.
BOBBY: I'll see ya around, kid.
SAM: See ya around.
SAM and BOBBY hug.
BOBBY: He gets in... You fight him tooth and nail, you understand? Keep swingin'. Don't give an inch.
SAM: Yes, sir.
As Bobby lay dying in the hospital bed, it's Sam who grasps Bobby's hand and thanks him though.
From Bobby, we learned that idjits can mean I love you.
Those are all serious heartwrenching moments with Sam and Dean. I also liked Bobby as a crazy old book-hording, alcoholic coot who kept the hunting world running in as organized a fashion as possible.
I liked Weekend at Bobby's
because we got to see him going through what probably passed as an ordinary weekend. A little B & E...
A little lying to law enforcement...
A little recipe sharing...
And working around the clock to find answers for seemingly unsolvable problems. Here's to the man in the battered hat.
I miss you, old man.
All caps from homeofthenutty