Buddy Holly — 1959 Winter Dance Party Tour

The ill-fated tour began on 23 January 1959 in Milwaukee

Waylon Jennings and Buddy Holly photographed in a photo-booth in Grand Central Station, New York City, in January 1959 —Image Public Domain via Wikimedia.

23 January, 1959 was the start of the “Winter Dance Party” rock’n’roll tour and its first show would be at the Million Dollar Ballroom in Milwaukee. The tour was scheduled for 24 dates, ending on 15 February, and followed a gruelling schedule with gigs every night across three states, in towns and cities that were often hundreds of miles apart.

Yet despite the freezing temperatures of these Midwest states close to the Great Lakes, thousands of fans still turned out and paid the $1.50 admission to see the shows.

It could be described as the tour from hell, as everything that could go wrong, did go wrong. The worst of it was when the three headliners Buddy Holly, Ritchie Valens. and The Big Bopper, JP Richardson were killed in a plane crash on February 3.

Even before that catastrophic event, the omens weren’t good. They were booked on one of the most poorly organized tours in the history of rock music.

The buses, which were old worn out Trailways passenger buses, broke down regularly. Five were replaced, and with heaters not working properly, the acts resorted to burning newspapers in the aisles to try to keep warm.