Kerouac Wore Khakis: Ghost of the Beat Writer Stars in 1993 Gap Advertising Campaign

“When [Jack] Ker­ouac died in 1968 at the age of 47, he was a bro­ken alco­holic, his lit­er­ary rep­u­ta­tion so deplet­ed he was unable even to find a paper­back pub­lish­er for his last nov­el, Van­i­ty of Dulu­oz,” writes The Tele­graph. “Unsure of what val­ue to put on his estate, the bank val­ued it at a nom­i­nal $1. Over the years, it would rise to an esti­mat­ed $20m.” As The Tele­graph goes on to describe, the Ker­ouac estate start­ed gen­er­at­ing its wealth when, dur­ing the 1990s, feud­ing rel­a­tives, exer­cis­ing ques­tion­able author­i­ty over the writer’s lit­er­ary remains, began auc­tion­ing things off. The orig­i­nal man­u­script of On The Road was sold to James Isray, own­er of the Indi­anapo­lis Colts, for $2.43 mil­lion. John­ny Depp paid $50,640 for Kerouac’s rain­coat, tweed over­coat and oth­er per­son­al belong­ings. And pho­tos were licensed off to cor­po­ra­tions.

Enter the Gap’s 1993 “Ker­ouac Wore Khakis” adver­tis­ing cam­paign. The cam­paign drew on images tak­en in 1958, when Jer­ry Yuls­man fol­lowed Jack Ker­ouac around Green­wich Vil­lage, tak­ing pic­tures for Pageant Mag­a­zine. (See orig­i­nals here and here.) 35 years lat­er, Madi­son Ave. mar­keters air­brushed the images, stripped them of col­or, and, some­how found a way to graft onto stodgy pants, worn by desk jock­eys nation­wide, the illu­sion of free­dom. That sleight of hand would make Don Drap­er proud. As for what hap­pened in Ker­ouac’s grave, we can only con­jec­ture.

We’ll have more from the annals of com­mer­cial­iz­ing the Beats tomor­row.

Relat­ed Con­tent:

Jack Kerouac’s Naval Reserve Enlist­ment Mugshot, 1943

Bob Dylan and Allen Gins­berg Vis­it the Grave of Jack Ker­ouac (1979)

Jack Kerouac’s Hand-Drawn Cov­er for On the Road

Ker­ouac Reads from On the Road (1959)