When Andy Warhol first became famous, few knew what to make of his art. When Apple first released the Mac­in­tosh — dra­mat­i­cal­ly pro­mot­ed with that Rid­ley Scott Super Bowl com­mer­cial — few knew what to make of it either. The year was 1984, when almost nobody had seen a graph­i­cal user inter­face or even a mouse, let alone used them, and the Mac­in­tosh looked as strange and com­pelling when it entered the com­put­ing scene as Warhol did when he entered the art scene. Both seemed so casu­al­ly to repu­di­ate so many long-held assump­tions, an act that tends to star­tle and con­fuse old­er peo­ple but makes imme­di­ate sense to younger ones. What hap­pened, then, when Warhol and the Mac­in­tosh first crossed paths?

Jour­nal­ist David Sheff, who wrote an ear­ly pro­file of Steve Jobs and con­duct­ed the last in-depth inter­view with John Lennon and Yoko Ono, remem­bers it well. In Octo­ber 1984, he and Jobs attend­ed the ninth-birth­day par­ty thrown by Ono for Sean, her son with Lennon. As a present, Jobs brought along one of his com­pa­ny’s new Mac­in­tosh­es and set it up him­self in young Sean’s bed­room. “Sean took con­trol of the mouse, and rolled the small box along the floor,” Sheff writes. “Steve said, ‘Now hold the but­ton down while you move it and see what hap­pens.’ Sean did, and a thin, jagged, black line, appeared on the screen. Sean, entranced, said, ‘Cool!’ He clicked the mouse but­ton, pushed it around, and on the screen appeared shapes and lines, which he erased, and then he drew a sort of lion-camel and then a fig­ure that he said was Boy George.”

Though Boy George may not have been in atten­dance, the par­ty’s unsur­pris­ing­ly fab­u­lous guest list also includ­ed Andy Warhol (an “eccen­tric uncle” to Sean) and Kei­th Har­ing, both of whom Sheff remem­bers com­ing into the room as part of a crowd want­i­ng to catch a glimpse of Sean’s new toy. It was­n’t long before Warhol, pre­sum­ably com­pelled by the artis­tic impulse as well as by his fas­ci­na­tion for all things new, asked if he could give it a try:

Andy took Sean’s spot in front of the com­put­er and Steve showed him how to maneu­ver and click the mouse. Warhol didn’t get it; he lift­ed and waved the mouse, as if it were a conductor’s baton. Jobs gen­tly explained that the mouse worked when it was pushed along a sur­face. Warhol kept lift­ing it until Steve placed his hand on Warhol’s and guid­ed it along the floor. Final­ly Warhol began draw­ing, star­ing at the “pen­cil” as it drew on the screen.

Warhol was spell­bound – peo­ple who knew him know the way he tuned out every­thing extra­ne­ous when he was entranced by what­ev­er it was – glid­ing the mouse, eyes affixed to the mon­i­tor. Har­ing was bent over watch­ing. Andy, his eyes wide, looked up, stared at Har­ing, and said, “Look! Kei­th! I drew a cir­cle!”

In his diary, Warhol writes of enter­ing Sean’s room to find “a kid there set­ting up the Apple com­put­er that Sean had got­ten as a present, the Mac­in­tosh mod­el. I said that once some man had been call­ing me a lot want­i­ng to give me one, but that I’d nev­er called him back or some­thing, and then the kid looked up and said, ‘Yeah, that was me. I’m Steve Jobs.’ ” But Jobs, pos­sessed of as keen a pro­mo­tion­al instinct as Warhol’s own, assured him that the offer was still good, and that he would also give him a les­son in draw­ing on the Mac right then and there. “I felt so old and out of it with this young whiz guy right there who helped invent it,” writes Warhol, not­ing that “it only comes in black and white now, but they’ll make it soon in col­or.”

The Mac­in­tosh made an appear­ance in Warhol’s “Ads” series of paint­ings in 1984, the same year he also agreed, accord­ing to Art­sy’s Abi­gail Cain, “to be a spokesper­son for Apple’s rival in the per­son­al com­put­ing sphere — Com­modore. The artist was to pro­mote the company’s new com­put­er, the Ami­ga 1000, and its cut­ting-edge mul­ti­me­dia capa­bil­i­ties” that includ­ed a 4,096-color dis­play. At the machine’s launch, Warhol “used ProPaint to sketch Blondie lead singer Deb­bie Har­ry in front of a crowd of eager tech enthu­si­asts,” which you can see in the video above. Just a few years ago, the efforts of dig­i­tal artist Cory Arcan­gel and spe­cial­ists at Carnegie Mel­lon Uni­ver­si­ty recov­ered 28 long-lost dig­i­tal paint­ings Warhol made on his Ami­ga. Whether the artist ever made any­thing with or even took deliv­ery of his promised Mac, we don’t know – or at least we don’t know yet.

Relat­ed Con­tent:

Short Film Takes You Inside the Recov­ery of Andy Warhol’s Lost Com­put­er Art

Andy Warhol Dig­i­tal­ly Paints Deb­bie Har­ry with the Ami­ga 1000 Com­put­er (1985)

Apple’s Guid­ed Tour to Using the First Mac­in­tosh (1984)

Dis­cov­er the Lost Ear­ly Com­put­er Art of Telidon, Canada’s TV Pro­to-Inter­net from the 1970s

Japan­ese Com­put­er Artist Makes “Dig­i­tal Mon­dri­ans” in 1964: When Giant Main­frame Com­put­ers Were First Used to Cre­ate Art

Based in Seoul, Col­in Mar­shall writes and broad­casts on cities and cul­ture. His projects include the book The State­less City: a Walk through 21st-Cen­tu­ry Los Ange­les and the video series The City in Cin­e­ma. Fol­low him on Twit­ter at @colinmarshall or on Face­book.