GUEST: When I was a little kid, my parents got it at a yard sale in Chicago.

They were looking for a salt shaker for their brand-new house, but they saw this there for five dollars, and they just had to get it.

And ever since then, it's just been on the wall in our house, and I've just always been curious about it.

APPRAISER: Do you know when your parents bought it?

GUEST: Well, I was about one at the time, so I think, like, '98, '99.

APPRAISER: Well, the painting is by an artist named, uh, Gertrude Abercrombie.

It's signed and dated, 1945, oil on panel.

GUEST: Okay.

APPRAISER: She is known as a bit of a bohemian artist, a Surrealist, and she worked in Chicago.

GUEST: Okay.

APPRAISER: So it makes sense that you would find it there.

She also has a lot of s, associations with jazz.

Dizzy Gillespie actually played at her second wedding.

GUEST: Oh, wow.

APPRAISER: She's known for these Surrealist paintings.

She considered them somewhat of a self-portrait.

And we know that, she said that-- I'm not making it up.

(both chuckling) In this particular painting, we can see the owl.

There's the moon...

GUEST: Mm-hmm.

APPRAISER: ...and the cloud, the cup on the table there.

The proverbial witch's brew.

GUEST: Mm-hmm.

APPRAISER: She had trouble with alcohol, as well, so I, I think we see aspects of her vision of herself as kind of a, a witch, a character outside of, uh, the normal.

GUEST: That's really interesting.

APPRAISER: And it's all in a very barren place.

I think at auction, even though it's only four by five inches, uh, we would give it an estimate of $8,000 to $12,000.

GUEST: Wow, wow, that, that's a lot.

APPRAISER: More than five.

GUEST: That's... (chuckles) I would, I would have guessed, like, maybe $35.

APPRAISER: Yeah.

GUEST: Wow.

APPRAISER: Her work is quite rare and it's also on a major upswing.

Her strongest prices are all within the last five years.

GUEST: Wow.