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Old Victorian Inns in Connecticut seem to bring out Dean's sharp tongue. Must be the "fish out of water" scenario. When Scooby Doo comes on the brain though, all bets are off.
"Old school haunted houses you know? Fog and secret passageways, sissy British accents. Might even run into Fred and Daphne while we're inside. Mmm. Daphne. Love her."
How about when they saw the dolls for the first time? Nothing is sacred in the world of Supernatural.
"Wow! This is a lotta dolls. Er, they're nice, they're not super-creepy at all."
"We are so screwed."
Best line ever.
Houses of the Holy
When faced with the idea of angels, which to Dean at the time was like accepting Santa Claus or the Easter Bunny was real (or Unicorns!), Dean manages to share conventional wisdom.
"Well I learned a valuable lesson here...always take down your Christmas decorations after New Year's, or you might get filleted by a hooker from God.”
Folsom Prison Blues
Dean needs to setup a fight for a diversion. He uses his sensitive people skills to get to the core of the biggest goon in the room.
"I wanted to ask you, because I couldn't help but notice you're two tons of fun, just curious. Is it like a thyroid problem or is it some deep seeded self-esteem issue? 'Cuz you know, they're just donuts, not love."
What Is and What Should Never Be
All that needs to be mentioned is the word "Genie" and Dean's mind is gone.
"My God, Barbara Eden was hot, wasn't she? And way hotter than that Bewitched Chick."
All Hell Breaks Loose Part II
After 22 years, the horrific deaths of his mother and father, not to mention getting his little brother killed, Dean has avenged his family by killing with the Colt the big bad himself, yellow eyes. As he and Sam marvel over the corpse and take in the shocking events that just happened, Dean's words are profound.
"Check that off the to do list."
Coming up, seasons three and four.
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