So, I'm writing up Dean's canon history, and good god, y'all, there's a lot of it. Like, stupid amounts. So I made an outline.
Need I say that if you're not current with canon, there will be SPOILERS? I will just in case. HEY PEOPLE THERE WILL BE SPOILERS.
A) I am Born
o Fate's a Bitch, or The Impala of Destiny
o In the Key of Things that Suck, or Mom, you're not a Ceiling Fan: The Day that Ruined My Life
B) Crappy Childhood - or, How John Winchester was a Bad Father
o My Own Prime Directive: Protect Thy Brother
o Band on the Run: A tale of Modern Day Nomads
o Not Even the Snoopy Dance Could Make This Better: Another Crappy, Dadless Motel Christmas
o Yeah, this is a Healthy Childhood: My training as a Shotgun Wielding Ghostbuster
o I Iz Literate, or Dean Winchester gets his GED Because School is for Losers and Sammy
o There's No Business but the Family Business, or, My Way or Fuck You: John Winchester's Rules for Life.
C) The Band Breaks Up - Sam Goes to College and Dean Drinks the Kool-Aid
D) The Interregnum: Coping with Sam Away, which Dean didn't do so Well
E) The Disappearance of One John Winchester - AKA, Season One
o What's with the CW and Stanford? Or, Happy Halloween, I'm fucking up Sam's Collegiate Life
o The Death of Sam's Squishy Jessica Moore, who was also Not a Ceiling Fan
o Creepy Things Go Bump and Are Killed by Winchesters
o Dean is a Wanted Man, and not just by Fangirls - Shapeshifter Round One, or, hey, sweet, I’m legally dead.
o We're Not Going to Talk About the Racist Truck, but Dean once dated a chick for three whole weeks, dude, get the Guinness Record people on the phone
o The Internet is for Porn and Idiots: How we Met the "Ghostfacers"
o The Return of John Winchester -- Why were we Looking for him again? He's kind of a douche
o My Daddy Issues, Let me Show you Them, along with my inherent insecurities
o The Colt of Wonder, and the Crash of Doom
F) The Plight of Dean - The Guiltening - AKA, Season Two
o It's a Family Tradition: John's deal with Azazel to save Dean's Life.
o No more Daddy makes Dean and Angsty, Guilt-Ridden Boy
o Hey, Dean, your brother might go darkside and it he does you’ll have to kill him, or: thanks, Dad, like I really needed THAT to think about
o OH GOOD GOD CLOWNS, THEY ARE NOT YOUR FRIENDS NO MATTER WHAT YOUR DADDY TELLS YOU!!! Also, bonjour, Ladies Harvelle.
o The Winchesters kill more baddies and Dean has more merrily promiscuous sex
o Brush with the FBI in Bmore, setting up incoming legal woes
o Attack of the Mandroids: Our Homage to Inside Man -- Enter Special Agent Henrickson
o Azazel's Telathon Kids: The Merry Band of Demon-Blood Drinking Misfit Psychics
o My Brother is a Psychic, this will End Well
o Too Precious for this World: Bobby is the Original Marriage Ref, or Fuck You, Trickster Part One
o Battle Royale the Supernatural Version
o The Death and Life of Sam Winchester, or Gimme my Brother and I’ll give you my Soul
o Fuck you Azazel, you’re deady-dead dead
G) The Final Countdown’s Not Just a song on the Monster Rock CD, AKA Season Three
o For the Reord: Canon implies I start this season with a hot-chick threesome.
o Way to Go, Dumbass - or how the Winchesters fucked things up by opening the Devil’s Gate
o Maury says you're not the Father, or, DEAN WINCHESTER HAVE YOU NEVER HEARD OF CONDOMS?
o Ladies Night: Never Trust a Demon, Sam, you fucking Moron; and also Sexy British Occult Thieves who want to bone Dean and the Sams that fantasize about them
o Holy Crap little kids are scary, or That Time we Re-enacted the Shining
o My Daddy Issues, Let Me Show You Them Again: or, Dreams Suck Out Loud
o Once more, with Feeling: Sam wants to save Dean but Dean isn't having it! Again some more!
o Co-Dependency: A Case Study - Mystery Spot
o Round One: Sam, you shouldn't trust a Demon, or Hi, Dean, my name is Ruby
o Holy Crap, Creepy Christmas Pagans in their Creepy Christmas Sweaters
o I'm Batman, or Lucky Rabbits Feet can kiss my Ass
o Dean Winchester has a Mouth like a Sailor -- Ghostfacers Part Deux
o I don't want to die
o Henrickson goes Kablooie - or Lilith is a creepy, CREEPY little girl
o No, really, I'd rather not go to Hell, that sounds like a terrible idea
o A New-Found Empathy for Milkbone; or that time that I was torn to shreds by Hellhounds
H) How I spent my Summer Vacation: An amusing recollection of pain, suffering, and my eventual apprenticeship as a demonic torturer, by Dean Winchester
I) Apocalypse Right Fucking Now, or There’s an Angel in my Outfield, AKA, Season Four
o Castiel’s Timely Groping
o Get a Little Crazy - 66 Seals and no Heidis in site, or Freshness Guaranteed for a Limited Time
o Luke or Annakin, the Sam Quandry
o Monster Mash: Pennsylvania's weird
o I don't want to talk about the masturbating suicidal teddy bear. Seriously, dude, what the hell?
o Round Two: Sam is a Lying Liar who Lies, or I know you're still boning the demon, cut it out
o Angels are better than Deloreans: My Blast to the Past and How it Went Horribly Awry
o Catharsis isn’t Always Good: The Torture of Alastair and the Big Reveal
o Lord, take This Cup Away From Me: Dean’s Guilt Groweth
o Fun and Prophet: The Day that Sam and Dean learned about Rule 34, or The Gospel According to Dean Winchester isn't just a joke anymore
o Lilith is a Skanky Hose Beast -- tell me something we didn't know.
o I Love You, I Hate You: Continuing In-depth Coverage of Sam and Dean's relationship
o For Your Own Good: A Very Winchester Intervention
o Lose Your Illusions: Or, Yes, You Angels are Dicks
o On my Signal, Unleash Hell - Or, I told you your girlfriend was a bitch
K) Ain’t Nobody’s Angel Condom, Aka, Season Five
o Castiel chose Team Awesome: The Littlest Angel done good
o The Break-Up Redux: Sam and Dean go their separate, man-painy ways
o Sam and I pinky-swear not to get possessed by Lucifer and Arch Angel Michael respectively
o War -- HUH -- What is he Good For, or The Horsemen Cometh
o The Tricky Trickster: Or, Family Exposition Heavenly and Not
o Fuck the Fourth Wall: Cosplay for the Masses at the Supernatural Fan Convention
o The Death of Jo and Ellen, no pithy title here because that sucked
o The Trouble with Bobby and He-Witches
o OK Cupid: Divined by Fate, or Back to the Future Part II
o So Hungry: Famine Rideth and he's seriously jacked-up looking
o The Second Detox of Samuel Winchester and how it broke my heart
o Zombies aren't all Fun and Games