GUEST: This is a Bob Dylan poster that was inserted into Bob Dylan's Greatest Hits albums in 1967.

And the poster was designed by a very famous graphic artist by the name of Milton Glaser.

Milton Glaser also designed the "I Love New York" logo.

And I have been collecting Bob Dylan, uh, memorabilia for many years now.

And, uh, I found out that Milton Glaser, back in 2018, would sign my posters if I sent them in to him.

APPRAISER: And he just did that for free?

GUEST: No, it, it was a $50 donation to one of three organizations that Mr. Glaser supported.

And I sent in my posters and, with proof of, uh, $150 donation.

And within seven days, my posters were returned, and, uh, they are signed.

APPRAISER: Now, before you had Milton Glaser sign these, where did you get them from in the first place?

GUEST: My wife and I have been antiquing for many years.

And of course, there were many times I found the album, but without the poster.

Three times, I struck gold and found the albums with the posters.

APPRAISER: It is designed by Milton Glaser, who was really one of the great graphic designers of the late 20th century.

And the poster is one of the most beloved and most famous rock posters of all time.

And I think that, in the design world, they look at it as an icon of 20th-century design.

The poster not only looks great, it reads great.

The font, called Babyteeth, is something Milton Glaser designed, and it really stands out.

This album came out in 1967, and one year later, it went gold.

And at least 500,000 were printed in the first year.

Now, 500,000 copies of anything is a lot.

It's a lot of albums, it's a lot of royalties for Dylan, and it was a lot of posters that everybody who bought this album had, put it up on their dorm room walls.

If I'm not mistaken... (chuckling) ...if I can break the fourth wall here just for a second- I understand that somebody who's directing this segment may have had this poster on their wall when they were growing up.

I mean, this poster was everywhere.

GUEST: That's right.

APPRAISER: When these went up on dorm room walls, when students moved to other dorms, the posters most often came down and were either thrown out or didn't move on with them.

Now, a question for you.

When you bought the album with the poster in it, how much did you pay for the album?

GUEST: Ten, $15, $25.

APPRAISER: When I did a little research just before coming out to speak to you, I found copies of the album available for sale for $50.

GUEST: Mm-hmm.

APPRAISER: And they have the, the, the sticker on it, the, the sizzle sticker that says "contains the full-color Dylan poster."

So you can buy the album and the poster for $50.

Have you ever seen a signed poster before?

GUEST: Well, yes, the other two that I have.

(laughs) APPRAISER: So a handful have come out of the woodwork.

GUEST: Uh-huh.

APPRAISER: They're all signed in the multicolor crayon.

And recently, when these posters have come up at auction, they've been estimated between $1,500 and $2,000.

GUEST: (chuckling) Very nice.

Thank you very much.

APPRAISER: You're very welcome.

GUEST: It's been a wonderful experience, and, uh, I'm going to be keeping Dylan.

(chuckles)