Whether we lived through them as kids or as grown-ups, few of us feel sure about whether we miss the 1990s. No gen­er­a­tion did more to define the decade before last, at least in the West, than the unmoored, irony-lov­ing, at once deeply cyn­i­cal and deeply earnest “Gen­er­a­tion X” that suc­ceed­ed the wealth­i­er, more influ­en­tial Baby Boomers. No writer did more to define that gen­er­a­tion than Dou­glas Cou­p­land, the Cana­di­an nov­el­ist, visu­al artist, and seer of the imme­di­ate future whose 1991 lit­er­ary debut Gen­er­a­tion X: Tales for an Accel­er­at­ed Cul­ture gave the cohort its name. There he wrote of the twen­tysome­things who lived through the 1990s def­i­nite­ly not as kids, yet, frus­trat­ing­ly, not quite as grown-ups, com­ing hap­less­ly to grips in the mar­gins of a human expe­ri­ence that an advanced civ­i­liza­tion had already begun detach­ing from sup­posed expec­ta­tions — jobs, hous­es, sta­bil­i­ty, tight con­nec­tion between mind and body, unques­tion­ably “real” lived expe­ri­ence — of gen­er­a­tions before.

Cou­p­land, also a pro­lif­ic sculp­tor (next time you get to his home­town of Van­cou­ver, do vis­it the some­how always strik­ing Dig­i­tal Orca), writer of the film Every­thing’s Gone Green, star of the doc­u­men­tary Sou­venir of Cana­da, and now the devel­op­er of a snor­ing-assis­tance smart­phone app, knows a thing or two about switch­ing media. Five years after break­ing out with Gen­er­a­tion X, he also made Close Per­son­al Friend, the not-quite-cat­e­go­riz­able short about tech­nol­o­gy, mem­o­ry, and iden­ti­ty at the top of the post. In what plays as a cross between a Chris Mark­er-style essay film and a mid­dle-peri­od MTV music video, Cou­p­land con­tin­ues his career-long rumi­na­tion about our “accel­er­at­ed cul­ture” and the fas­ci­nat­ing­ly empow­ered yet com­pro­mised human beings to which it gives rise. What does it mean in this mod­ern, hyper­me­di­at­ed con­text, he won­ders, that we now won­der whether we actu­al­ly have lives? “Not hav­ing a life is so com­mon,” he says. “It’s almost become the norm. […] Peo­ple just aren’t get­ting their year’s worth of year any­more.”

Giv­en our cul­ture’s fur­ther accel­er­a­tion since he spoke those words in 1996 — the world wide web as we know it hav­ing got its start just three years before — Cou­p­land’s thoughts on the sub­ject, whether expressed in fic­tion, through sculp­ture, or onscreen, still sound plen­ty rel­e­vant. Close Per­son­al Friend, with its void­like back­drops, video-blender edit­ing, and scat­tered clips of whole­some mid­cen­tu­ry Amer­i­cana, bears the aes­thet­ic mark of its era. Cou­p­land’s faint­ly omi­nous talk of “FedEx, Prozac, microwave ovens, and fax machines” also time-stamps it tech­no­log­i­cal­ly and cul­tur­al­ly. But the obser­va­tions have car­ried through, only grow­ing sharp­er, to his lat­est work. Asked to imag­ine the “two dom­i­nant activ­i­ties” of life twen­ty years hence, the Cou­p­land of 1996 names “going shop­ping and going to jail,” pur­suits he sees as now merged in his essay col­lec­tion pub­lished last year, Shop­ping in Jail. Just above, we have a half-hour con­ver­sa­tion between Cou­p­land and Q host Jian Ghome­shi about his even new­er book, a study of mis­an­thropy in nov­el form called Worst. Per­son. Ever. In the talk, he cites “I miss my pre-inter­net brain,” a slo­gan he made up that has gained much trac­tion in recent years. But does he real­ly? “No,” he admits. “It was bor­ing back then!” Close Per­son­al Friend will be added to our col­lec­tion of 675 Free Movies Online.

Relat­ed Con­tent:

Watch Free Online: Richard Linklater’s Slack­er, the Clas­sic Gen‑X Indie Film

The Always-NSFW Kevin Smith and Jason Mewes Catch Up in Jay and Silent Bob Get Old Pod­cast

Col­in Mar­shall hosts and pro­duces Note­book on Cities and Cul­ture and writes essays on cities, lan­guage, Asia, and men’s style. He’s at work on a book about Los Ange­les, A Los Ange­les Primer. Fol­low him on Twit­ter at @colinmarshall or on Face­book.