(jazz piano) ♪ Blues, blues stay away from me ♪ ♪ Blues, blues, blues, won't you let me be ♪ ♪ I've got some money, got my honey ♪ ♪ Ain't no misery in me ♪ ♪ I got a ranch in Arizona ♪ ♪ A yacht in L.A., a house in San Francisco ♪ ♪ Overlooking the Bay ♪ - [Narrator] People who hear singer Rebecca Kilgore say she has one of the sweetest voices they've ever heard.

♪ Some money, I've got my honey ♪ - [Narrator] Tell that to her face and she gets a little bit embarrassed.

- And I'm (laughs) far more critical than you are.

But people have said, oh, it's like cream or butter or all these fattening things.

But (laughs) I just want to sing as straightforwardly from my heart as I can.

♪ Bet on the horses, don't care if I lose ♪ ♪ I take a trip to Paris or any place I choose ♪ As few embellishments as possible.

I just want to sing the way I speak.

♪ Ain't got no blues ♪ ♪ 'Cause there ain't no misery in me ♪ - [Narrator] It's the kind of voice that really knows how to caress the melody and lyrics of classic tunes from the '40s and '50s.

And what does Rebecca look for in a song?

- Well, certainly lyrics and melody.

I'm a real melody person and I think, even, a melody might capture me first, but it's got to have something good to say.

I'm generally an optimist, so I don't sing too gloomy or whiny songs.

- [Narrator] No torch songs for you?

- Not too many.

And so I like to impart some joy and optimism to my audience, so I want to be generally upbeat.

♪ Nothing's impossible I have found ♪ ♪ For when my chin is on the ground ♪ ♪ I pick myself up, dust myself off ♪ ♪ Start all over again ♪ ♪ Don't lose your confidence if you slip ♪ ♪ Be grateful for a little pleasant trip ♪ ♪ Just pick yourself up, dust yourself off ♪ ♪ Start all over again ♪ - [Narrator] A fixture on the Portland jazz scene for many years it seems like everyone wants to work with Rebecca.

Ukulele Maestro Lyle Ritz.

♪ My breaking heart and I agree ♪ ♪ That you and I could never be ♪ ♪ So with my best, my very best ♪ ♪ I set you free ♪ ♪ I wish you well ♪ - [Narrator] Young singer-bass player Kate Davis.

♪ To every word of love I heard you whisper ♪ ♪ The raindrops seem ♪ ♪ The raindrops seem ♪ ♪ To play a sweet refrain ♪ ♪ Though spring is here ♪ ♪ To me it's still September ♪ - [Narrator] And, of course, her longtime musical partner, Dave Frishberg.

(music) ♪ Here am I, surrounded ♪ - [Narrator] As much as a natural as Rebecca seems to be, she never planned to become a singer.

In college see majored in art, then dropped out and was working as a secretary/computer programmer.

- I had been a kind of a closet guitar player and singer, very shy, and I moved to Portland in about 1979.

And one thing led to another.

I became friendly with a band and there was an opening in that band and I tried out for it and the rest is history.

Yeah, I thought it was a fun experience.

I really, really enjoyed it.

I was new to Portland, so here were some instant friends.

The music community in Portland is like a fraternity.

It's very supportive, and I met wonderful people.

And I just thought, wow, this is a lark.

This is fun.

And I was happy to be a singing secretary.

- [Narrator] But in the '90s, she needed to make a career choice.

- I was then doing a gig two nights a week, Wednesdays and Thursdays, at the Heathman Hotel with Dave Frishberg on piano.

And I loved it.

And it was great.

It was rewarding, enriching.

People seemed to enjoy it.

I was learning new material and it was really fun.

And then I would go to work the next day and it was a very nice job.

I have nothing against the job.

I was working as a secretary at Reed College then, but I would be thinking about the music and every once in a while I would be called back to my job and, oh, yeah.

And it became, like, an inconvenience to be at my work.

And it felt like jumping off a cliff.

But at that time, I was willing to take the risk.

And it's worked out.

♪ Won't be long ♪ And there were what's called sit-down gigs where a band would be hired as a steady a certain night a week or nights a week at one place.

And that was a very secure feeling.

It wasn't like it is now.

There are fewer of those kinds of gigs in Portland.

♪ Good bye ♪ - [Narrator] And to prove it, Rebecca took us on a tour of her old haunts.

- This used to be a place called Father's.

And it opened up in Portland in about 1980-something, early '80s.

And it was the place.

It was newly renovated and stylish and hip.

It was just the place to go.

And they had live music there.

And I was happy to be in the band that they hired, a quartet called Wholly Cats.

And we were the house band.

And I have so many wonderful memories.

- Must have been heartbreaking when it closed.

- It was, it really was.

And I can't go in there now.

- Really?

- No.

I just can't make myself go in there, 'cause they probably changed it all.

♪ Just pick yourself up, dust yourself off ♪ ♪ Start all over again ♪ - Okay.

So behind us is the Big Pink.

- Yeah, and on the 33rd floor, a wonderful place I used to perform at, used to be called Atwaters, beautiful view.

And Mel Brown and his group played there on weekends.

And I sang there with Dave Frishberg every Wednesday.

It was wonderful.

And now it's the Portland City Grill.

- Now it's for people to go and eat.

- Right.

I can't go there either.

♪ Pick yourself up, dust yourself off ♪ ♪ Start all over again ♪ - This was the Jazz Quarry, the famous Jazz Quarry.

- The hot spot in Portland for many, many years before I lived here, it was a hang.

It was where all the Portland musicians hang.

Just a great homey place.

- So sad to see it all gone.

- I don't even recognize it now.

I think we're in the right place.

♪ Pick yourself up ♪ ♪ Take a deep breath ♪ - [Narrator] Of all the places that have shut down, I think this is the saddest.

- This really is.

This was the crown jewel of Portland.

This is the first venue I ever sang at in Portland with the quartet that I was in, Wholly Cats.

And I thought I was in a movie.

It felt so glamorous, and- - It was all Art Deco, the black and white.

- Beautiful.

- And Silver.

- I was on top of the world when I performed there.

It was a dream come true.

♪ And start all over again ♪ ♪ Start all over again and again ♪ (audience applauding) - [Narrator] Since she doesn't have a regular gig in Portland, Rebecca has to spend a lot more time working on getting hired elsewhere.

- It's a wonderful way to make a living.

And when I do perform, I'm well paid.

But, boy, there are dry spots and that's really scary.

- [Narrator] However, it has enabled her to work with some amazing talent from around the country.

- [Rebecca] This is Johnny Frigo.

He is a fantastic jazz violinist.

That is me with Jon-Erik Kellso.

He's a wonderful trumpet player who lives in New York.

- [Narrator] And when there's not an immediate gig on the calendar, Rebecca works on finding that next great song she wants to learn.

She and Dave Frishberg made a CD of the songs of Frank Loesser.

And her latest project is a CD of songs about love.

- "Hooray for Love," take one.

♪ Love, love, hooray for love ♪ ♪ Who is ever too blase for love ♪ ♪ Make this a night for love ♪ ♪ If we have to fight, let's fight for love ♪ ♪ Some sigh and cry for love ♪ ♪ Ah, but in Paris, they die for love ♪ ♪ Some waste away for love ♪ ♪ Just the same hooray for love ♪ - [Narrator] But wherever she sings and however often she sings, she knows she's lucky to be doing what she loves.

♪ Go down with love ♪ ♪ Just take it away, away, away ♪ - But, you know, way back when I was a teenager, I never even dared to dream that I could do it.

It was just something tucked away.

- [Narrator] Well, I think so many musicians and so many audience members are glad that you did dare it.

- Yeah, I am too.

I really am.

(upbeat jazz music) ♪ I got my trousers pressed, shoes shined ♪ ♪ I had my coat and vest relined ♪ ♪ Take a look at my lapel, see the flower ♪ ♪ Can't you tell I'm happy as the day is long ♪ ♪ I haven't got a dime to lend ♪ ♪ I got a lot of time to spend ♪ ♪ Just a pocket full of air feeling like a millionaire ♪ ♪ I'm happy as the day is long ♪ ♪ Got a heavy affair and I'm having my fun ♪ ♪ Am I walking on air ♪ ♪ Gee, but I'm the lucky one ♪ ♪ I've got my peace of mind, knock wood ♪ ♪ I hear that love is blind, that's good ♪ ♪ Because the things I've never seen ♪ ♪ Never seem to worry me ♪ ♪ I'm happy as the day is long ♪ (no audio)