Brandy - The Looking Glass
Obvious choice, but thank goodness I really like the song.

Little Room - White Stripes
Considering my tiny home and my big ambitions, this song makes the list.

Well you're in your little room
and you're working on something good
but if it's really good
you're gonna need a bigger room
and when you're in the bigger room
you might not know what to do
you might have to think of how
you got started sitting in your little room

I'm Hip - Blossom Dearie
This is on the list because not only do I dig Dearie's voice, and it's a sweet tune, but because I am so the type to sing a song about how cool I am.

I'm hip. I'm no square.
I'm alert, I'm awake, I'm aware.
I am always on the scene.
Makin' the rounds, diggin' the sounds.
I read Playboy Magazine.
'Cuz I'm hip.

Like, dig! I'm in step.
When it was hip to be hep, I was hep.
I don't blow but I'm a fan.
Look at me swing. Ring a ding ding.
I even call my girlfriend "man,"
I'm so hip.

Every Saturday night
with my suit buttoned tight and my suedes on
I'm gettin' my kicks
watching arty French flicks with my shades on.

I'm too much. I'm a gas.
I am anything but middle class.
When I hang around the band,
poppin' my thumbs, diggin' the drums,
squares don't seem to understand
why I flip. They're not hip like I'm hip.

I'm hip. I'm alive.
I enjoy any joint that's where there's jive.
I'm on top of every trend.
Look at me go. Vo-dee-o-do.
Bobby Darrin knows my friend. I'm so hip.

I'm hip, but not weird.
Like, you notice, I don't wear a beard.
Beards were in but now they're out.
They had they're day. Now they're passe.
Just ask me if you're in doubt,
'cuz I'm hip.

Now whatever the fads
And whatever the ads say is neatsville
I'll be keeping abreast
Out in front of the rest with elitesville

'Cuz I'm cool as a cuke.
I'm a cat, I'm a card, I'm a kook.
I get so much out of life.
Really, I do. Skoo ba dee boo.
One more time play "Mack the Knife."
Let 'er rip. I may flip, but I'm hip.

Woo oooh, I'm hip.
Mmmmmm, I'm hip.

Night Train - Xavier Cugat
Killer instrumental song, that makes me want to dance certain steps to it as I walk down the street listening to it.

Is That All There Is? - Peggy Lee
A dark song, but I like dark, and I love the devil-my-care chorus:

Is that all there is, is that all there is
If that's all there is my friends, then let's keep dancing
Let's break out the booze and have a ball
If that's all there is

Still working on it....