Kentucky Avenue (Blue Valentine)...My son has Cystic Fibrosis and when he was an infant I was giving him chest therapy one day and this song was on my headphones, and I broke down and started crying my guts out.
I Wish I Was In New Orleans (Small Change)...Bittersweet ode to a town and time now gone, but which wasn't then.
Better Off Without A Wife (Nighthawks at the Diner)...need I say more than the title? Beers of refusal.
The Piano Has Been Drinking (Not Me) (Small Change) "you can't find your waitress with a geiger counter, and she hates you and your friends but you cannot get served without her..." There is, or was, a very good YouTube clip of him performing this on Fernwood Tonight back in the 70s.
Bad Liver and a Broken Heart In Lowell (Small Change)...Kerouac-inspired hymn to lost love and death by alcoholism, featuring the classic lyric, "I don't have a drinking problem, except when I can't get a drink," and "The moon ain't romantic, it's intimidating as hell."
Martha (Closing Time)...one of those songs where, when you listen to it, it puts you somewhere else. In this case, the mind of a lovelorn middle aged man whose who is married with children and still secretly pines for his highschool love, 30 years gone.
Goodnight Irene (Orphans Disc Two)...this is a cover of, I think, a very very very old Leadbelly song. Waits makes it his own and when it's over it takes about three more minutes to snap out of the cast spell. "Sometimes I take a great notion to jump in the river and drown."
In The Neighborhood (Swordfishtrombones)...sluggishly singsong ode to suburbia with melodic complaints about noisy delivery trucks, stray dogs, and bothersome contruction work.
Bottom of the World (Orphans Disc One)...old-timey ode to hoboing and broken noses. "The best friend you'll have is a railroad track."
Never Let Go (Orphans Disc Two)...words can't really say how exquistite this is. References to pawned wedding rings, jumping to one's death, and walking home through the mud. A beautiful piano line with highschool marching band drumfills and accordion flourishes. Perfect.