1959 Gibson Sunburst Les Paul
Notable owner: Ace Frehley (Kiss)
Estimated price: $800,000

Decades of guitar design hit a highpoint in 1959 with Les Paul’s Gibson Sunburst. This particular specimen was blessed with a particularly wide “flame” in the grain of the maple wood that makes up its body. Its value leaped further when Frehley, lead guitarist for Kiss, bought the guitar from a vintage guitar shop in Manhattan, paying $3,500. The store’s owners later bought it back for $1,000 more than they sold it. In the early ‘90s, the instrument sold for just $16,000, but its value has soared since.

1965 Fender Stratocaster
Notable owner: Stevie Ray Vaughan
Price at auction: $623,500

“Lenny” was named after Vaughan’s wife Lenora, who picked the guitar up for the then unknown Stevie Ray as a 26th birthday present. Although it was a badly refinished pawn shop find, the Strat with the artsy inlay became famous in SRV’s hands. It became a celebrity-finding snowball along the way. First the guitar got a new neck, given to Vaughan by ZZ Top guitarist Billy Gibbons. Then Vaughan had a chance encounter with Mickey Mantle at a Houston Astros game, and when he couldn’t locate a bat for Mantle to sign, Vaughan offered up his guitar instead. It was purchased by the music chain Guitar Center at the 2004 Clapton auction at Christie’s.

1958 Gibson Explorer
Notable owner: Eric Clapton
Estimated value: $500,000

The guitar Clapton trotted out to play “Rita” and “Have You Ever Loved a Woman” at the Royal Albert Hall in London on September 21, 1983, is one of only 19 experimental Explorer models Gibson released in 1958. Clapton bought the angular instrument from a fan in Austin, Texas not long before he made it famous onstage that night. In 1999 the guitar sold to an unknown buyer for $120,000 at auction at Christie’s, part of a nearly $5 million sale of Clapton guitars and equipment. These days, experts say, the Explorer would fetch four times that.

Custom Rosewood Fender Telecaster
Notable owner: George Harrison
Price at auction: $434,750

When Fender wanted to add a solid-body Rosewood Telecaster to its catalogue, it shipped a custom prototype to Harrison in December 1968 — flown to England in its own seat next to a courier — in hopes that it would jump-start sales. When Harrison played it in the famous impromptu concert on the roof of the Apple studio the next January, the guitar became an instant icon. A year later, Harrison gifted the guitar to the singer/songwriter Delaney Bramlett, who sold the guitar in 2004 at an auction at Juliens for nearly half a million dollars.