GUEST: I brought with me several small pieces that were gifted to my mother by Ed Ruscha, the artist.

She was living in the West Village in New York City, uh, in a little apartment on Bleecker Street, a two-bedroom with four people living in the apartment.

Her roommate's mother was friends with Ed Ruscha's mother, uh, from Oklahoma, and he was returning from a trip from Europe.

He needed a place to stay.

Her mother reached out to, mother-to-mother, said, "Can Ed crash on your sofa?"

He stayed with them for a few days while he waited for his, uh, car to be delivered from Europe.

While he was there, he gave them this piece and this one, and then later, uh, wrote these letters to them, and, uh, gave my mom this piece, which is actually a, a drawing of her car.

She had gotten in a fender bender, and the funny story behind that is that the woman who she had run into immediately got out of the car and walked up to her and, you know, extended her hand to shake her hand and said, "It's so nice to meet you."

(chuckles) And so the copy that he put on there is pretty playful.

He kind of made a mock ad and talks about, it's a great way to meet people, is to get into minor collisions in your VW.

The visit was in the fall of 1961, and then the letters' postmark is December.

So they stayed in touch for a couple of months after.

I think she was curious and wanted to get them, uh, authenticated.

And so she looked up his gallery and wrote to the Gagosian Gallery, and sent a letter with photocopies of them.

And apparently, they forwarded it to Ed.

And she got a voicemail message from his studio manager saying, "Yes, Ed remembers you, and he remembers those pieces."

APPRAISER: Ed Ruscha is one of the most important artists of the 20th century.

He was born in Omaha, Nebraska, in 1937 and spent a lot of his time in Oklahoma City, but in 1956, moved to Los Angeles.

So we really think of him mostly as a California artist.

What I find really fascinating about this group is that we are seeing the early stages of him playing with text... GUEST: Mm-hmm.

APPRAISER: and words.

His best-known works today are paintings and drawings of words.

He has taken something as simple as a word and elevated it... GUEST: Mm-hmm.

APPRAISER: raising it to a level that makes you stop... GUEST: Mm-hmm.

APPRAISER: and think a little bit deeper about language and culture.

Some of his most important paintings from the early '60s were of the word "scream."

GUEST: Mm-hmm.

APPRAISER: And I don't know if this was the first time he utilized "scream," but it certainly was, was very early.

We have two letters here.

There's a smaller one that's still in the envelope, which is pencil on paper.

And then we have on display here the larger letter.

My first reaction was, these are also works of art.

He's using different-color marker for different words.

He puts that ampersand right in the center, very bold.

And so visually, it's very interesting.

GUEST: Mm-hmm.

APPRAISER: This one closest to me is a self-portrait of Ed Ruscha.

GUEST: Mm-hmm.

APPRAISER: It’s watercolor and graphite on paper.

I don't think I've ever seen a self-portrait that he made.

GUEST: Mm-hmm.

APPRAISER: Tell me a little bit more about, uh, the, the advertisement that he gave and left behind to your mom and the roommate.

GUEST: Mm-hmm.

This was an ad that he had designed and that he's actually in.

That's him, the cowboy.

The thought bubble that he customized it with is the names of my mom and her roommates.

APPRAISER: Ed Ruscha has museum shows and is shown by some of the most successful galleries in the world.

And so his notoriety and desirability continues to grow.

This letter that we see here, I would put an auction estimate of $3,000 to $5,000.

The smaller sheet, which is in the envelope still, I would put an auction estimate of $2,000 to $3,000 on that letter.

GUEST: Hm, okay.

APPRAISER: The self-portrait, $10,000 to $15,000.

GUEST: Okay.

APPRAISER: The collage, also $10,000 to $15,000.

GUEST: Okay.

APPRAISER: And then we have the drawing of the Volkswagen car.

This one really, you can see where the jump-off points were for the rest of his career.

GUEST: Mm-hmm.

APPRAISER: Where he's dealing with cars and text... GUEST: Mm.

APPRAISER: and all of the things that we really come to recognize as being what he is best known for.

An auction estimate on this I would suggest should be $20,000 to $30,000.

GUEST: Great.

(chuckles) Wow.

That's great.