I’m guessing at the date this was released seeing as it was on his album Easy Tiger, which came out in 2007. I can find zero information about this music video. All I know is that it exists because there it is posted above. It must be footage from some public domain 1970s TV Show. That’s my best guess.
I never really cared what the song meant, but it obviously had to do with drugs since Ryan Adams is known for having come off of a long history of drug abuse around this time. I did find somebody who has the definition of what a “Halloweenhead” is from Ryan Adams himself here. But who cares about that? What does Urban Dictionary say “Halloweenhead” means?
The first person just quoted lyrics from the song.
The second person got it right. The song is the Ryan Adams & The Cardinals version of White Punks On Dope by The Tubes. It’s a song about their fans.
The third person said it is “the act of giving or receiving head on halloween. Should be annual event that everyone participates in.” My favorite is their sample sentence: “Dude, i just got some hella nice halloween head.” I don’t think that saying is going to catch on.
The fourth person has the best definition:
“A deer who is a gigantic coke-head, spends all day trying to buy bags and then just blowing line after line after line. Also gets heavily involved in the pharm-game.”
They are in the ballpark–unlike number 3. However, I think their sample sentence is questionable:
“When that one deer wandered into our room he could tell almost immediately that the deer on the wall was a ginourmous halloween-head.”
This is the actual definition that apparently appeared in one of the posts Ryan Adams had/has on his website:
“A fan of The Cardinals music. stoner. outcast. someone who doesn’t know what kind of mood they are in. Not sponsored by Bud Lite or collecting girls or guys numbers during a quiet breakdown. usually are laid back and engage in mellow conversation with band members when seen in arcades or getting food. Don’t ask for shit when people are eating. not gravity challenged but reality challenged. also known as Bed-Heads, or Chandler Bings.”
With that in mind, I guess the people in this music video fit that definition pretty well.