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Rare rock memorabilia from Holly, Cobain, heads to auction

Heritage puts Kurt Cobain’s watch and Buddy Holly’s last signed item up for auction on Oct. 4, 2008.

When the only watch that Kurt Cobain was ever photographed wearing goes on the block at Heritage Auction Galleries in Dallas, Oct. 4-6, it will be joined by an equally rare and singular offering in the form of the last autograph that Buddy Holly ever gave.

The two stories behind these rock rarities couldn’t be more different, but the two men behind them both share certain unquestionable distinctions: Both defined their eras in rock music. Both were tremendous talents in unlikely packages, and both were cruelly taken in their musical prime.

A macabre duo, perhaps, but one that is right at home in the Heritage October 2008 Signature Music & Entertainment Memorabilia Auction, which also includes the Glen Ford Collection containing items from the Ford estate that have a direct connection to Marilyn Monroe, another tragic figure gone far too soon.

The last record signed by Buddy Holly

It was Monday night, Feb. 2, 1959: The lineup at the Surf Ballroom in Clear Lake, Iowa, included Buddy Holly, Ritchie Valens, The Big Bopper (J.P. Richardson), Dion and The Belmonts and Frankie Sardo.

“Good night! We’ve got a plane to catch, but we’ll be back in spring!” Holly declared after his final song, “Brown-Eyed Handsome Man.”

As the young musicians were leaving the Surf Ballroom, a teenager from Clear Lake named Jim Anderson — waiting patiently between the dressing room and the exit — persuaded Holly, Valens, the Bopper, and the other performers, to sign the Buddy Holly 45 rpm vinyl record he received as one of the first fans admitted through the Surf’s door that night.

It was late, approximately 12:20 a.m. Buddy, Ritchie Valens and the Bopper then hopped into a car driven by the Surf’s manager, leaving at approximately 12:30 a.m., arriving at the Mason City airport at 12:40 a.m. Within 25 short minutes, the trio would be tragically killed in a fiery plane crash.

The last known item to be autographed collectively by Holly, Valens and the Bopper is this teenager’s signed 45 single. Only one other autographed 45 from that evening is known to exist. Those signatures, however, were acquired between sets.

Items from Buddy’s last performance are not really rare. They’re non-existent. The Surf Ballroom performance was scheduled at the last minute — there was simply no time to prepare any promotional posters or handbills. The 45 singles of Holly’s new release “It Doesn’t Matter Anymore”/”Raining In My Heart” were the only items handed out as promotions for that final show.

This signed 45 resonates with the personalities of these legendary musicians, whose careers were cut short minutes after they signed it. This is a truly singular piece of rock and roll history... so historic, in fact, the signed 45 was showcased in the 2000 BBC documentary “Rock Shrines — Buddy Holly,” featuring Jim Anderson’s son, Scott Anderson, detailing the night’s events while holding the precious 45, encased in a 12.5" x 12.5" double-sided frame.

Jim Anderson gave the 45 to Scott in 1997 — a strikingly appropriate gift, as Scott took over management of the Surf Ballroom the previous year.

Certified as authentic by PSA/DNA, the autographed 45 also has the blessing of Buddy Holly authorities Randy Steele and Bill Griggs, as well as Holly fans and experts around the world.

The 45 was also signed by Dion (of The Belmonts), his bandmate, Carlo Mastrangelo, and accompanying act Frankie Sardo. Included with the lot is a letter of authenticity from Scott Anderson tracing the history of the piece, from his father’s encounter with the musicians on that trag