Buddy Holly and Waylon Jennings Photo Booth Photographs in New York, probably January 1959

This is a set of two photo booth pictures likely taken at Grand Central Station in New York in 1958-'59. Holly was 23 and Jennings was 22. One is a g-rated shot of two pals having a smoke. The other depicts a deadpan Holly flipping the bird in front of Waylon's face. I don't know, there is something heartwarming about these pictures. I guess it's that geniuses are people too. These fantastic photos have been colorized and printed as full-sized giclees.

Size: About 19" x 23"
Condition: Mint

The shots were likely taken in Grand Central Station in New York, in late 1958 or early 1959 during some Waylon Jennings recording sessions Holly was producing.

Shortly after, Jennings took a train to Chicago to meet up with the band for the ill-fated "Winter Dance Party Tour."

The tour began in the brutal midwestern winter, and the buses kept breaking down. Holly decided to charter a plane from Fargo ND to Minnesota for himself, Jennings and another band member, Tommy Alsupp. JP Richardson, aka "The Big Bopper," had the flu and asked Jennings if he could have his seat. Richie Valens also talked Alsupp out of his. A few minutes after their 1:50 AM takeoff from Mason City Airport, the plane crashed and no one survived.

Both pieces are available separately, links below.

Bird flip one is Poster #1
G-rated one is Poster #2