One poster represents the end of an era; the other, the very beginning (or close enough). They are bookends of a sort, each a delicate, yet concrete keepsake from a historic moment. These printed original vestiges with handwritten annotations should not exist, yet here they are in the same auction, no less, appropriate, since one man here profoundly influenced the other. One poster hails from Feb. 3, 1959, the day Buddy Holly, Ritchie Valens and the Big Bopper, J.P. Richardson, were killed in a plane crash near Clear Lake, Iowa, on their way to a show in Moorhead, Minn. The musicians were en route to the Moorhead Armory as part of the Winter Dance Party tour when their single-engine Beechcraft Bonanza crashed in a cornfield. This is the only known poster from a concert that inexplicably wasnt canceled The Day the Music Died, as Don McLean famously called it in American Pie. The other comes from what The New York Times Robert Shelton called a memorable evening of new songs by an incredibly gifted song writer (and) a young giant April 12, 1963, when 21-year-old Bob Dylan played his first major concert at New Yorks Town Hall. The poster itself is rare enough; this one comes with Dylans scribbles, asides and signatures, the digressions of the jokerman. Four years earlier, on Jan. 31, 1959, Dylan, then still Robert Zimmerman of Hibbing, Minn., had seen Holly at the Duluth Armory. Holly looked me right straight dead in the eye, and he transmitted something, Dylan wrote in his Nobel Prize acceptance speech in 2016. Something I didnt know what. And it gave me the chills. Holly and Dylan are reunited in Heritage Auctions Friday, Saturday, and Sunday, Nov. 11, 12, and 13, Music Memorabilia Signature Auction. These particular posters have never been available at auction and might well prove among the most valuable ever offered. These are two extraordinary items, either one of which would be the centerpiece of any auction, says Pete Howard, director of Concert Posters. Ive told many colleagues I cannot imagine having a pair of posters like this in a single event ever again. Heritage has offered a Winter Dance Party poster only once, in the spring of 2020, when previously unseen cardboard from the Jan. 25, 1959, show at the Kato Ballroom in Mankato, Minn., realized $125,000. The poster in the November auction had originally been affixed to a telephone pole in advance of the 12th stop on the tour but fell to the ground; there are no pinholes, just the residue of the sticky material used to keep it in place. The maintenance man who found it placed the poster in a closet, face down, and forgot about it for 50 years. Decades later, it was sold to a poster dealer who then sold it to Jim Cook, its current consignor. This poster was created as a so-called tour blank by the legendary Murray Poster Printing Co. of New York. Unlike its Mankato counterpart, which has the show information printed in the space above the musicians names and photos, the Moorhead Armorys name, the concert date and the two showtimes (7:30 + 9:30) were written in red grease pencil, which was common practice. There are five known Winter Dance Party posters. This is the only one known for the show Holly, Valens and the Big Bopper never made. Astonishingly, the show went on without the men killed shortly after takeoff. Bobby Vee, then all of 15, performed Hollys songs, because he knew all the words. Waylon Jennings ultimately filled in for his friend for the tours final two weeks. To think, rock bands today move stadium shows because one member has the flu, stated Howard. Here, the top three headliners died, and the show went on. Unbelievable. The sheer poignancy of seeing that date on the poster, Feb. 3, and how the venue box is filled in so casually by hand adds to the window cards impact. Four days before that scheduled show in Moorhead, Dylan and his best friend, Louis Kemp, drove to Duluth in Kemps fathers 1958 Buick to see Holly. It was brutally cold: With the windchill, Kemp wrote in his autobiography, (it) was minus 44 degrees. But young Bob was a fan and couldnt be kept away. I have always believed that a spiritual connection of some kind was forged that night between Buddy Holly and Bobby Zimmerman, though no one in the crowd was aware of it, wrote Kemp. I only know what I saw, and it looked a lot like a torch being passed. Four years later, Dylan played to about 1,000 people at New York Citys Town Hall. His 24-song set list that night included Blowin in the Wind, A Hard Rains A-Gonna Fall, Dont Think Twice, Its All Right, Masters of War and Boots of Spanish Leather. In The Times the following day, Shelton wrote that Dylan was a folk musician who breaks all the rules of song writing except those of having something to say and saying it stunningly. The songs are among the best written in this countrys folk vein since Woody Guthrie stopped composing. Handbills from this historic occasion have been sold at auction before. Posters from the Town Hall show are exceedingly rare; there are three known to have survived the journey from 1963. There is but one of these Dylan-decorated posters, a Holy Grail long hidden from the public. He also added something at the bottom of the poster concerning the record label that was to release his second record, The Freewheelin Bob Dylan, a month later. Where it says only Columbia Records, Dylan added: is a drag. This poster has a backstory unparalleled in my 30-year history with concert posters, according to Howard. This isnt just any good musician. This isnt just any concert poster. And this isnt just any autograph. For all the reasons mentioned above, this is among my favorite concert posters. If I could have just one concert poster for the rest of my life, this would be it. To learn more, visit www.HA.com.