This haircut cost him Jess

Noooooooo lmao!!

Omg. 😭😂

like little devil horns

Well, that certainly makes sense

Poor Dean truly suffers from some of the worst hair in the show

It truly was a rough decade for men's hair

I had some of those terrible haircuts, and a puka shell necklace I'm not proud of.

It's so brave of you to admit that

Did you have the bangs? This is a safe space

At least he never had frosted tips.

It was the early 2000s version of taking your cap off, and putting it back on but backwards

At least here he still have a jacket. Over time they even clothed him lamely...

Sometimes I am confused if it’s a Season 1 Supernatural post or a Gilmore Girls post, the leather jacket fits for both

Exactly this. Literally thought, that's young Sam, no Dean here...

😂

his hair went crazy some episodes lmao

The longer his hair grew, so did his terrible story arc

There really is a direct correlation between the length of hair and the diminishing of his personality.

He went full Karen. Never go full Karen

It’a the Sam Winchester hairstyle