Hi, i'm making a playlist for my younger brother, and I wanted to put a Mountain Goats song on their, but it should be very specific. He's pretty confident, and I wanted to put a song on their where John is particularly boastful about himself, as I think he'd respond to this well, but I'm not really sure which song to choose.
Can anyone please suggest one in particular?

I'm not sure what you mean by "boastful" as he rarely sings about himself, and even when the narrator does it's not usually in a positive manner. So here are some songs that I would describe as "confident" and/or "shouty". In no particular order:

Commandante
This Year
Letter from Belgium
Going to Georgia
Going to Scotland
Jaipur
Baboon
Prana Ferox (just because it rocks)
Genesis 19-1-2
New Chevrolet in Flames
Love Cuts the Strings
The Best Ever Death Metal Band in Denton
No Children
See America Right
Oceanographer's Choice
Against Pollution (what's more boastful than bragging about shooting someone in the face with a shotgun?)
Heretic Pride (what's more boastful than bragging about being burned at the stake?)
Lovecraft in Brooklyn
Psalms 40:2 (what's more boastful than bragging about burning down a church?)
Estate Sale Sign

(Man, I just skipped through pretty much the whole discography. That was a lot of fun. Now I need to listen to half those albums all the way through.)

Dunno if they fit, quite, but Up the Wolves and Orange Ball of Peace also are pretty fuck you, even if it's a defence.

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midgoat

I think Dtrom's list is pretty good ("confident and/or shouty" lol) but I am shocked to find The Story of the Pigs Who Ran... etc. missing!

Lest we forget Quito?

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A fly can't bird but a bird can fly.

Yeah, I don't know why I left off Pigs... and Up the Wolves, but Quito was a legitimate oversight of which I am sorry.

Always New Chevy in Flames and Up the Wolves forever.

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[www.last.fm]

Maybe you could use You Were Cool...to say you always thought he was cool?

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We are the ones who don't slow down at all...

The Day the Aliens Came.

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"But not me,
I'm gonna crawl,
I'm gonna crawl,
I'm gonna crawl,
Back to the sea."

"Goddamit, I love John Coltrane."

it's not an original, but the boys are back in town might be a good and fun addition.

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The first thing that distinguishes a writer is that he is most alive when alone. - Martin Amis