Bobby:
- Bobby's Weekend Off by emebalia. Gen. Summary: Sam: "You built a panic room?"; Bobby: "I had a weekend off." 4x02 ; This is said "weekend". It took Bobby a little while longer than a weekend to build the Panic Room, though. Mind the warnings.
https://www.fanfiction.net/s/8350911/1/Bobby-s-Weekend-Off

- With Blood by Mirrordance. Gen. Summary: Bobby Singer was just a friend to a widower, not minding the occasional babysitting. But his devotion for the Winchester family truly began when he was struck by a terminal illness and saved only by a sacrifice from Dean. Pre-Series.
https://www.fanfiction.net/s/5365066/1/With-Blood


Castiel:
- Impressive at the Time by crOwnlEssG. Gen. Summary: Tag to 6x20 - Castiel's first ever act of disobedience.
https://www.fanfiction.net/s/6995427/1/Impressive-at-the-Time

- Set Me Free by miss_annthropic. Pre-slash. Summary: “I’m the one who gripped you tight and raised you from perdition.” There was a story there… this is it.
http://miss-annthropic.livejournal.com/80282.html


Dean:
- Apple Pie and Chevrolet by Swellison. Gen. Crossover. Stanford era. Summary: Jim Ellison and Dean Winchester meet at Cashmere's Apple Harvest Festival when they're both asked to judge the apple pie contest.
https://www.fanfiction.net/s/7545127/1/Apple-Pie-and-Chevrolet#

- Flagstaff by NongPradu. Gen. Pre-series. Summary: Sam runs away from home. Dean and John try to find him. Mild spoilers for 5.16 - ther consequences Sam didn't know about.
https://www.fanfiction.net/s/6359331/1/Flagstaff


Sam & Dean:
- Scales by annonwrite. Gen. Summary: Pain scales are good, except when they aren't.


Benny
- O Brother, Where Art Thou? by emebalia. Gen. Summary: "This human was probably my only chance to get out of Purgatory. Better not letting him get killed." Dean and Benny in Purgatory, Benny's POV. Warning: A vampire's mind is a dark place.
https://www.fanfiction.net/s/9295349/1/O-Brother-Where-Art-Thou

I have a tag on my pinboard for my headcanon fics HERE (https://pinboard.in/u:oppisum/t:Personal:headcanon/), if that helps. There's Gen, Destiel, Wincest, and Wincestiel (I have head different headcanons for each, eek!). I hope this is sort of what you're looking for.

Second Glance by ygrawn (http://ygrawn.livejournal.com/5703.html)

In my head Dean/Sam OTP head canon, I always believed that Bobby knew. This fic is a 'John knows' and it made me realise that, of course he did.

Thanks for the recs, guys! This should keep me busy for a while. :)

oppisum: I also have different headcanons for different pairings.

Edited 2014-03-18 05:45 pm (UTC)

Jep - "Dean used to play the Piano" makes it so in my hc!

Riding a Bike http://fanfiction.net/s/3048661 (http://fanfiction.net/s/3048661) For my hc ´cause Dean and kids=awnsome!

Warning! In my native languages yet it´s only translate to S6 and really - I hat the end of this! So this is for now my perfect ending:
Numinous verse http://scyllaya.livejournal.com/26116.html (http://scyllaya.livejournal.com/26116.html)


Hope I haven´t misread your request.

Edited 2014-03-19 12:45 pm (UTC)

For me, that's anything gaelicspirit has written.