Not sure which way to go with this, but it's probably best to ease him in, so I'd go with safe stuff like:

Spoon - Girls Can Tell
Pavement - Crooked Rain, Crooked Rain
Dismemberment Plan - Emergency & I
Wilco - YFH
Elliott Smith - either/or

Looking at a little less safe:

Refused - The Shape of Punk To Come
Fiery Furnaces - Blueberry Boat
Archers of Loaf - Icky Mettle
Bedhead - WhatFunLifeWas
Neutral Milk Hotel - In the Aeroplane Over the Sea