Craigslist Crapshoot

Welcome to Craigslist Crapshoot, our weekly search for the most bizarre, awesome, and/or terrible vehicles that the online classifieds has to offer. 
(EDITOR’S NOTE: Due to the site outage last week which prevented comments on a butt-load of posts, we’re re-running the last Craigslist Crapshoot to give you all a chance to play. Sorry about the down time, now let’s get our searches on!)
We got all 21 Jump Street last week two weeks back, looking for the coolest cars under $2,000 that a High Schooler might want to drive. We’ll see which ad most popped our quiz in a sec, but first let’s become true auto enthusiasts.
That oblique reference is of course from Jeremy Clarkson’s assertion that one cannot be a true car nut until they have owned an Alfa Romeo. I don’t know of that badge of honor is extended to the execrable rebadged Nissans from the ’80s, but we’ll take those and any other Alfa for sale – as long as the price doesn’t exceed $5,000. Yes, I’m expecting a sea of 164s and mountains of Milanos, but we want are cars that look like they might be worth the price of entry.
As always, we want your finds to go down in infamy and not in the site’s spam filter. Since we’ve changed commenting systems, you may need to update your commenter account. Make sure you have a Disqus account – they’re free and easy to get – and then comment away.

When I was in high school my ride was a Honda Express when it wasn’t raining and a 1961 Corvair 700 Turtle Top when it was. Yeah, I wasn’t the fastest kid around, nor was I the coolest. You all found some cool rides that today’s high schoolers would no doubt jones over, and many of them were practical as well.
The 2000 VW Jetta sporting a stick and a replacement VR6 found by Salguod was an early contender for the crown, but then I remembered owning one of these and what a turd it was. I wouldn’t want to saddle a pizza delivery driver or whatever it is teens do for money these days with what is likely to be a money pit.
I also liked Smalleyxb122‘s suggestion of a “Shaggin’ Wagon” to terrify parents, but as a parent myself, I couldn’t in good conscience perpetuate that stereotype. In the end it was Engineerd would took the prize, allowing a high schooler to fully embrace their own Wonder Years in a pre-disastered 1968 Buick Le Sabre that’s both cool and likely an easy ride to wrench on. It also uses regular gas which is a plus, and it has a back seat that’s big enough to sleep in if your parents start to really get all up in your grille about stupid stuff like grades and what you’re planning to do with your life.
Thanks to you all for helping out Generation… what are we up to now, Z? Congrats as well to Engineerd.