On Nov. 18, 19, and 20, with more than 700 lots of rich music history, Heritage Auctions realized nearly $2.1 million in a wide-ranging music memorabilia event that was led in part by some of America s most beloved musicians. The sale brimmed with significant concert posters, rare vinyl, a collection of personal items from the Grateful Dead s late co-founder Jerry Garcia, and a unique portrait painting of the king of parrotheads, Jimmy Buffett. Top honors in the event went to a 1959 concert poster that marks Buddy Holly & the Crickets' next-to-last performance and the band s last performance for which a poster was made. The historic "Winter Dance Party" poster sold for $250,000. It boasts a line-up of young hit-makers still on the ascent playing the Riverside Ballroom in Green Bay, Wis., on Sunday night, Feb. 1, 1959, two days before Buddy Holly, Ritchie Valens and J.P. The Big Bopper Richardson were killed in a plane crash on their way to the next show in Moorhead, Minn. That was The Day the Music Died. The few tangible keepsakes from that ill-fated tour, a scant handful of posters advertising the Winter Dance Party, have become among rock s most sought-after treasures. One sold at Heritage last year to become the world s most valuable concert poster at $447,000. Expectations were high, but we were pretty blown away that our Winter Dance Party became the third highest-priced concert poster in the history of the hobby, says Heritage s director of Concert Posters, Pete Howard. A quarter-million dollars is such rarified air, but this poster totally deserved it. The second highest price realized in the event came compliments of another unique offering: a beloved Jimmy Buffett painting, made for the 2011 New Orleans Jazz Fest, not only sold for a whopping $137,000, but proceeds from the sale go to the medical treatment for a 6-year-old with a rare medical condition. Garland Robinette, a gifted artist and beloved New Orleans media personality, painted a mustached Buffett into that Crescent City canvas because of its central place in the singer-songwriter's origin story. As Buffett put it in his 1998 biography, A Pirate Looks at Fifty, "The time I spent working and living in the French Quarter in 1967 changed my entire life," and he described being "a hippie and a musician," busking for spare change on street corners. In the painting, a figure lurks in the background, walking past and glancing back, Jimmy checking in on his younger self. Official prints made from this painting sell for big bucks, and the painting was celebrated upon its debut as Jazz Fest's poster in 2011. An iconic Skeleton & Roses poster advertising the Grateful Dead s Sept. 16-17, 1966, stint at San Francisco s Avalon Ballroom sold for $93,750, rightly so for one of psychedelia s most famous images. That s especially true of this first-printing poster, graded 9.8 Near Mint/Mint by CGC. It was among the most stunning examples of the poster Heritage has ever offered after setting the record, time and again, for this Family Dog masterpiece by Stanley Mouse and Alton Kelley. The Dead delight hailed from the renowned collection of celebrated poster collector David Swartz, who has spent years tracking down posters featuring psychedelic bands and venues. The three-day auction also featured a collection of personal items from the life and artistic career of Dead co-founder Jerry Garcia. The treasure trove was consigned by Vince and Gloria DiBiasi, Garcia s longtime personal assistants. About the DiBiasis, the Dead's bass player, Phil Lesh, writes in his book Searching for the Sound: My Life With the Grateful Dead, The DiBiasis were a steadfast, loving couple, with grown children, who had formed the only real constant in Jerry's life (other than his music) throughout the turbulent comings and goings of girlfriends, his illnesses, and the demands on his time and energy from every direction imaginable." The archive highlights included Garcia s personal sketchbook (which sold for $10,000), his briefcase with personal items (also $10,000), a double-sided drawing by Garcia ($9,375) and a pair of his beloved Ray-Ban sunglasses ($8,125). Other auction highlights included a 1968 Jimi Hendrix "Flying Eyeball" concert poster, the most iconic concert poster image for the American great and this one signed by its artist, Rick Griffin, which sold for $55,000; a Beatles-signed Please Please Me Mono UK first pressing record sleeve, which sold for $40,000; and a sealed and slabbed first pressing of the scarce, beloved and infamous 1987 The Black Album from Prince, graded 9.0, which sold for $25,000. Complete results from this sale can found at www.HA.com/7309.