The Two-Wheel Versions Of Pappy Van Winkle Bourbon

Just before the bourbon boom took off around the turn of the millennium, I was a newly minted drinker, happily discovering brown spirits and the virtues of labels containing the magic words “small batch” and “barrel proof.” I particularly enjoyed a fine whiskey called Pappy Van Winkle, which my brother—a poor medical student at the time—always seemed to have rolling around in a crate in the back of his VW. We were oblivious that we’d be unlikely to imbibe it regularly—if at all—in the very near future. As the popularity of bourbon soared, Pappy became the stuff of legend. These days, you’ll need a private detective to source a bottle and a trust fund to buy one. Had I only known…

Like my history with Pappy Van Winkle, there are plenty of motorcycles that went virtually unnoticed before becoming highly desirable. Many motorcyclists have a list of these sorts of bikes; machines they liked when it seemed no one else did. Maybe these bikes were ahead of their time, or misunderstood, but now everyone wants one—as if to affirm your good taste and foreknowledge.

When I drank Pappy, I enjoyed it, but I didn’t think it was necessarily better than all other bourbons. I just liked it. True, I was 21 and had a barely refined palette. The motorcycles listed below are not the most exotic or special—or even the most expensive—but like Pappy, they’ve gone on to be desirable beyond what anyone, save the ones who “knew it all along,” could have predicted. Most of these bikes are far less rare than a bottle of Pappy Van Winkle; further proof that as far as predilections go, motorcycling is one of the sanest.

If ever a motorcycle can be described as classy, this is it. Timeless, elegant, and basically a sales flop, the initial fervor for the Ducati Sport1000 never materialized into units sold. The Sport1000 was on the market for three years before being axed. Michael Lock, then-CEO of Ducati North America, chuckles when asked about it. It was a bike that presaged the “post heritage” trend of café racers, bobbers, and scramblers by a few short years. As such, its modern components, stalwart air-cooled Dual Spark engine, and Pierre Terblanche design now demands a premium to lovers of classic style. Find one on eBay and it will cost twice what it did in 2007. If only I hadn’t been a poor English major in 2007.

Aprilia’s SXV is a 77-degree V-twin supermoto. It’s as cool as it sounds. Very un-supermoto-like, it features fuel injection, a steel trellis/pressed aluminum chassis, and an undertail exhaust. The thing was a real performer too—when the engine wasn’t blowing up. Sadly, conflagrating twins are one of the more maligned of all engine configurations. The SXV seemed a weird niche bike to Americans at the time, and its sales figures reflected that. Fortunately, reliability concerns are more easily forgiven when viewed retrospectively and in the glimmer of illogical desire.

For the past two decades, the masses have been crying for a race-rep V-4 Honda literbike, so it's ironic that Honda's last attempt bombed. Honda's flagship VF1000R was only around for two years before it got the axe. Based around the FWS1000 racebike, the big Veefer had hotter cams and a higher compression ratio than its more plebeian VF1000F sibling. It also had gear-driven overhead cams, which is to VF-Rs as desmo is to Ducatis. Unfortunately, the VF1000R was big. We're talking 600 pounds big. Consequently, it was not exactly a world beater. Other Honda V-4s, like the RC30 and RC45, were coveted from the start, but the VF1000R has had to age gracefully into desirability. Oddly, it's hard not to want a Honda V-4 with the patina of—dare we say it—mediocrity.

Motorcyclists are a notoriously conservative lot when it comes to innovation and out-of- the-box thinking. Suzuki learned its lesson the hard way. The RE5, produced from '74­ to '76, featured a liquid-cooled Wankel engine, but not much else to recommend it. Forty years later, that's all you have to say before a certain demographic of motorcyclist starts reaching for the checkbook. We all know the type. As if to reiterate its strangeness, Suzuki gave it a weird canister-shaped dash that looks like it might have been the original inspiration for the ooze canister from Teenage Mutant Ninja Turtles. It's like putting a "kick me" sign on the class nerd. But who cares? It's a Wankel-engined motorcycle.

Do you have particular bikes you loved before it became “The Cool Thing”? Add your comment below.