1. Suicidal Teddy Bear
Season 4, Episode 8 – Wishful Thinking
2. TV Land
Season 5, Episode 8 – Changing Channels
Thanks to the trickster, Sam and Dean found themselves stuck in various tv shows.
I’d post a video, but the whole episode is worth watching.
3. Ganesh Makes a Cameo
Season 5, Episode 19 – Hammer of the Gods
Well this was quite random.
4. Fight the Fairies
Season 6, Episode 9 – Clap Your Hands If You Believe...
When you’re hunting elves, fairies, and leprechauns, it can lead to some mishaps.
5. Dean Punches Cupid
Season 5, Episode 14 – My Bloody Valentine
6. Groundhog Day
Season 3, Episode 11 – Mystery Spot
Strange, and kind of funny. How many different ways can Dean die?
P.S. I skipped over seasons 1 and 2. These seasons seemed to be more straightforward and serious. If I missed any strange moments from these then let me know and I'll add them in future takes.