Songs:
Telephone Call From Istanbul - mmmmmm, Marc Ribot guitar solo
Innocent When You Dream
Yesterday is Here
Clap Hands
Way Down in the Hole
Album: Big Time (yep, total cop-out, don’t care. If a song appears on it, it’s better than the studio version, IMHO)
My favorite quote that may or may not have been said by Tom Waits:
Well ya play that tarantella all the dogs’ll start to roar
The boys all go to hell and then the Cubans hit the floor
They drive along that pipeline, they tango till they’re sore
They take apart their nightmares and they leave 'em by the door
Just in terms of which songs pop into my head most often:
Favorite Album: Nighthawks at the Diner
Most Important: I suppose you could say that Sword Fish Trombones is a transitional album from his beatnik era to the kind of stuff he still does more than 20 years later, which I characterize as the Devil’s Jug Band.
Never Let Go
Cold, Cold Ground
Ol 55
Picture in a Frame
In the Neighborhood
And I adore Alice. I just do. But trying to pick is like drowning kittens. So that’s today’s lot. Could be different tomorrow.
While I like all of Waits, I’m not as big a fan of some of his over-produced earlier albums with strings. I prefer his later, less polished sounding music, which ironically is probably heavily produced to give it its raw sound.
Another favorite: Going Out West
I love this so much.
Man, this is hard. For now, I’ll go with:
Tom Traubert’s Blues (I honestly don’t understand why this isn’t everyone’s favorite song from any artist ever, but I digress…)
Time
Down There by the Train
Fish & Bird
Step Right Up
As you can tell. I’m a big fan of the ballads. I’m already kicking myself for leaving Burma Shave off the list, and Singapore, and Whistln’ Past the Graveyard and Mr. Siegal…
Whittling it down to 5 songs is a cruel exercise in Sophie’s Choices and force me to make cuts between works of equally evocative quality and fall back to criteria no less arbitrary than how I happen to feel at this moment.
I love both Christmas Card from a Hooker in Minneapolis and $29.00 for their storytelling.
Shore Leave is amazing not just for its storytelling but also because its exotic instrumentation paints the story with such exotic color.
Johnsburg, Illinois is so tender and vulnerable and simple and honest stripped of all artifice. It’s 90 second brevity accomplishes all that a love song can do
Long Way Home is a latter-day masterpiece that evokes the push and pull between the comfort of home and a perpetual pull of wanderlust.
Album-wise, I like Swordfishtrombones because in addition to being smack dab in the middle of some of my favorite songwriting, it is a blend of his older traditional stuff with his more experimental stuff.
Ask me again tomorrow and I’ll likely come up with an entirely different results.
“It’s supposed to be hard. If it were easy everyone would do it. It’s the hard that makes it great.” -Tom Hanks, A League of Their Own.
It killed me not to include Diamonds on my Windshield, Martha, Heart of Saturday Night, Small Change, Tom Traubert’s Blues, Burma Shave, Gin-Soaked Boy, Johnsburg, Illinois, Trouble’s Braids, Singapore, Clap Hands, Hang on St. Christopher, Innocent When You Dream (the song that sealed the deal for me), Come on Up to the House, Face to the Highway, Kiss Me…
But hey - rules are rules. 
Johnsburg, Illinois
Down There By The Train
Never Let Go
The Fall Of Troy
Tom Traubert’s Blues
Take It With Me
Hang Down Your Head
I could keep going! 
Love me some Tom.