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Winter Dance Party tour and death (1959)

Holly vacationed with his wife in Lubbock and visited Jennings's radio station in December 1958. For the start of the Winter Dance Party tour, he assembled a band consisting of Waylon Jennings (electric bass), Tommy Allsup (guitar), and Carl Bunch (drums). Holly and Jennings left for New York City, arriving on January 15, 1959. Jennings stayed at Holly's apartment by Washington Square Park on the days prior to a meeting scheduled at the headquarters of the General Artists Corporation, which organized the tour. They then traveled by train to Chicago to join the rest of the band.

The Winter Dance Party tour began in Milwaukee, Wisconsin, on January 23, 1959. The amount of travel involved created logistical problems, as the distance between venues had not been considered when scheduling performances. Adding to the problem, the unheated tour buses twice broke down in freezing weather, with dire consequences. Holly's drummer, Carl Bunch, was hospitalized for frostbite to his toes (sustained while aboard the bus), so Holly decided to seek other transportation. On February 2, before their appearance in Clear Lake, Iowa, Holly chartered a four-seat Beechcraft Bonanza airplane for Jennings, Allsup, and himself, from Dwyer Flying Service in Mason City, Iowa. Holly's idea was to depart following the show at the Surf Ballroom in Clear Lake and fly to their next venue, in Moorhead, Minnesota, via Fargo, North Dakota, allowing them time to rest and launder their clothes and avoid an arduous bus journey. Immediately after the Clear Lake show (which ended just before midnight), Allsup agreed to flip a coin for the seat with Ritchie Valens. Valens called heads; when he won, he reportedly said, "That's the first time I've ever won anything in my life." Allsup later opened a restaurant/bar in Fort Worth, Texas, called Heads Up Saloon. Waylon Jennings voluntarily gave up his seat to J. P. Richardson (the Big Bopper), who had influenza and complained that the tour bus was too cold and uncomfortable for a man of his size.

The pilot, Roger Peterson, took off in inclement weather, even though he was not certified to fly by instruments only. Buddy's brother Larry Holley said, "I got the full report from the Civil Aeronautics – it took me a year to get it, but I got it – and they had installed a new Sperry gyroscope in the airplane. The Sperry works different than any other gyro. One of them, the background moves and the plane stays like this, and in the other one the background stays steady and the plane moves, it works just backwards. He could have been reading this backwards... they were going down, they thought they were still climbing."

Shortly after 1:00 a.m. on February 3, 1959, Holly, Valens, Richardson, and Peterson were killed when the aircraft crashed into a cornfield five miles northwest of Clear Lake shortly after takeoff. The three musicians, who were ejected from the fuselage upon impact, sustained severe head and chest injuries. Holly was 22 years old.

The report did not mention a gun belonging to Holly that was found by a farmer two months after the crash. Newspaper accounts of the gun discovery fueled rumors among fans that the pilot was somehow shot, causing the crash. Another curious finding at the crash was that Richardson's body was discovered nearly 40 feet (12 metres) away from the crash while the others were found in or near the wreckage. However, an autopsy done at the request of Richardson's son in 2007 found no evidence to support the rumors. Dr. Bill Bass, a forensic anthropologist at the University of Tennessee, stated that "There was no indication of foul play," and that Richardson "died immediately."

Holly's funeral was held on February 7, 1959, at the Tabernacle Baptist Church in Lubbock. The service was officiated by Ben D. Johnson, who had presided at the Hollys' wedding just months earlier. The pallbearers were Jerry Allison, Joe B. Mauldin, Niki Sullivan, Bob Montgomery, and Sonny Curtis. Some sources say that Phil Everly, one half of The Everly Brothers, was also pallbearer, but Everly said that he attended the funeral but was not a pallbearer. Waylon Jennings was unable to attend because of his commitment to the still-touring Winter Dance Party. Holly's body was interred in the City of Lubbock Cemetery, in the eastern part of the city. Holly's headstone carries the correct spelling of his surname (Holley) and a carving of his Fender Stratocaster guitar.

Santiago watched the first reports of Holly's death on television. The following day, she suffered a miscarriage. Holly's mother, who heard the news on the radio in Lubbock, Texas, screamed and collapsed. Because of Elena's miscarriage, in the months following the accident, some government authorities implemented a policy against announcing victims' names until after families are informed. Santiago did not attend the funeral and has never visited the gravesite. She later told the Avalanche-Journal, "In a way, I blame myself. I was not feeling well when he left. I was two weeks pregnant, and I wanted Buddy to stay with me, but he had scheduled that tour. It was the only time I wasn't with him. And I blame myself because I know that, if only I had gone along, Buddy never would have gotten into that airplane."