How'd You Lose That? 2000 Porsche Boxster 986 "S"

You don't have to be an expert in the automotive market to see how cheap used Boxsters have become -- it probably has something to do with Porsche stamped them out like boxes of number 2 pencils headed to your local dollar mart.  Various interweb sources claim something like 160,000 of the 986 designated convertibles left the factory, but you'll have to search harder and pay more for the 3.2 liter S version...or you could buy this next basic Boxster that has had an undocumented upgrade to the 3.2 liter flat-6 if you don't mind buying a Porsche that was built in Finland. Find this 2000 Porsche Boxster offered for $5250 in Mountain View, CA via craigslist.

ASC Convertible: 1985 Toyota Celica GTS

The 3rd generation (internally called A60) Celica was the final rear-drive chassis to use Toyota's Celica name.  The next generation used a transverse front-drive setup that has become a de facto standard for economy cars, but up through 1985 you could get a Celica from the factory with a longintudinal engine and right wheel drive.  The A60 generation also added rack-and-pinion steering for the first time and ASC (American Specialty Cars) were nice enough to modify a few of the coupe versions into a decent looking drop top. Find this 1985 Toyota Celica GTS offered for $5900 in Anaheim, CA via craigslist. Tip from Mike Jr.

Mullet Dryer: 1989 Dodge Dakota Sport Convertible

Pickup trucks are the working dogs of the automotive world...and for decades they were strictly form-follows-function work machines.  But then auto designers started to get creative to sell things like pickups that were built from cars (the El Camino and Ranchero) and even performance pickups (SVT Lightning...etc)..and Dodge even went as far as to built a convertible pickup truck...so you could haul junk to the dump and have your mullet air dried at the same time. Find this 1989 Dodge Dakota Sport Convertible offered for $3500 in Norwalk, NY via craigslist. Tip from Cory.

Like A Heavyweight M100 Elan: 1987 Cadillac Allanté

The Cadillac Allante (Allanté) was another attempt by one of the big three cash in on the allure of the European import; think Chrysler TC by Maserati or AMC Eagle Premier -- but with an accent in the name causing grief for search features and web indexing in the future.  I also can't help but draw comparisons to the '90s Lotus Elan -- also a two-seat front-drive convertible with an engine built in a different continent from the body, but the Allante packed an extra 1600 lbs (approx the mass of a full Regardless, this next version is offered for some spare change...but would it be worth it? Find this 1987 Cadillac Allanté offered for $1995 (or $1595) in Port Charlotte, FL via craigslist. Tip from Dascpcu.

Some Sorting Required: 1991 Lotus Elan M100

The Lotus Elan M100 was a wedge shaped convertible penned by Peter Stevens (Jaguar XJR-15, McLaren F1, Lotus Esprit, MG ZR, ZS, ZT & TF) and built in the UK from 1989 through 1995.  The Elan was later produced by Kia in South Korea under the name Kia Elan (and Kia Vigato).  The Elan was a pretty design and it used a lightweight chassis and a name borrowed from the historical Lotus archives...but it was powered by an Isuzu (and later Kia) 4-banger mated to the front wheels.  By all accounts it was one of the best handling front drive cars ever built...but it just seems wrong to suffer power-on understeer in a Lotus! Regardless, I find myself inexplicably attracted to the little two seater in red.  Find this 1991 Lotus Elan M100 here on eBay with zero bids and starting bid of $4500 in Citrus Heights, CA with 2 days to go.

Premium Vintage: 1999 Porsche Boxster

I hate paying premium price for anything...which is why I spend a large part of my day obsessing over used cars, scouring the web for cars that have depreciated into the basement and can be purchased with your coronavirus stimulus check.  However...there is something captivating about time capsule cars -- those which appear to have avoided the inevitable decay for dust thou art, and unto dust shalt thou return. This next car is old enough to legally drink in all 50 states but only has 33k miles on the odo and is offered for a "premium" price, but not an insane one.  Does the clean condition merit the premium price? Find this 1999 Porsche Boxster offered for $13999 in Palos Verdes, CA via craigslist.

Surviviorlet: 1999 Volkswagen Cabrio

Most cars have a bell shaped popularity curve, but have you ever noticed that some cars have almost a step function of popularity -- one minute they are all over the road and then suddenly they all just up and vanish.  This seems to have been the case for the legendary Volkswagen Mk 3.5 Cabrio -- which was styled to look like the Mk IV Golf (97-05), but used mechanical bits from the older Mk 3 Golf (91-98).  Maybe that's why they dropped off the face of the earth...15 year old parts when they were brand new...regardless, you don't see them very often and you certainly don't see them in this nice condition. Find this 1999 Volkswagen Cabrio offered for $2500 in Houston, TX via craigslist. Tip from Jeff.

5-Speed Manual Swapped R107: 1981 Mercedes-Benz 380SL

This next car is offered by the seller as a "project" but it is much nicer than 99% of the projects offered for sale...it passes smog and has a manual gearbox swapped behind the 3.8 liter V8.  Sure, it needs some cosmetic work on the interior and needs new rear glass, but the real kicker is that these R107 Mercedes-Benz coupes are so under-priced in the market compared to anything else with two seats and German build quality.  Buy one. Buy another.  Get a barn.  Make the news in 30 years. Find this 1981 Mercedes-Benz 380SL offered for $5500 in Concord, CA via craigslist.

Korvmaro Kustom: 1963 Chevrolet Corvair V8

The Corvair is one of the few aircooled classics from the 60s that you can buy for a reasonable amount of money and drive around everyday (helps if you live in a place that is easy on weather.)  It had an advanced independent rear suspension under that aircooled engine out back...but today everything is amok and this Corvair is powered by a front mounted small block V8 and features a stick beam rear axle!! I don't know if this is an upgrade or downgrade. Find this 1963 Chevrolet Corvair V8 offered for $16,500 in Longview, CA via craigslist.

Fun In The Sun: 2004 Nissan 350Z Touring Convertible

I hate to say it...but the Z33 generation Nissan 350Z hasn't aged well at all.  The interior surface coatings are about as durable as the coating on an M&M and the interior design (eg gauge color) has aged about as well as Miley Cyrus. Sure...there are some people who might find it attractive, but even Liam Hemsworth ditched his wrecked one for a new model.  However, they do offer a decent level of performance and can be had with a 6-speed manual gearbox and a rag top. Find this 2004 Nissan 350Z here on eBay offered for $11,600 in Chaplin, SC.

15k Mile Ragtop: 1992 Chevrolet Corvette C4 Convertible

There is something about an older car that is free from dirt/grime that just makes me happy...and it probably has something to due with the fact that most of my classics have been well used and abused.  This next car is shockingly clean on the underside for a 27 year old car and has about 500 miles per year on the odo...and the price is great?  What's the catch? Oh, its a C4 Corvette...which I'm sorta starting to like these days...am I getting old? Find this  1992 Chevrolet Corvette Convertible offered for $12,950 in Omaha, NE via craigslist. Tip from Rock On!

Piccolo Progetto: 1979 Alfa Romeo Spider

This next car comes as a tip from Matt C who writes; If all this needs is carpet, it's a screaming deal. Might be a big if, but running sub-$2000 Italian cars aren't easy to find anymore.  Find this 1979 Alfa Romeo Spider offered for $1900 somewhere near Atlanta, GA

LS2 V8 Powered: 2005 Chevrolet SSR

A few years back, when retro styling was all the rage, the guys at GM decided to break another glass ceiling in the automotive world.  They introduced what was probably the worlds first mass market convertible pickup truck (we will ignore the ill-fated Dodge Dakota Sport, but that was another ASC hack job, not to be confused with a car purposed built from the factory like a Ford Model A pickup.)  Regardless, the SSR was built on the Chevy Trailblazer platform and was motivated by a 6 liter version of the LS2 V8 and it was gloriously fast and retro (in contrast the Fords anemic Thunderturd from the same retro-era).  Although the styling left something to be desired, and the SSR had the torsional rigidity of a wet churro, a remarkable 24,000 were produced from 2003 through 2006, so expect them to be cheap in the coming years as the original owners trade them for something that can hold their mobility scooters. Find this 2005 Chevrolet SSR offered for $13,000 in Tucson, AZ via craigslist. Tip from FuelTruck.

Straight-6 Slushbox: 1963 Ford Falcon Convertible

I'm gonna put my flame suit on and say the following: the V8 and 4-speed is overrated. Every other classic '60s American car that I see running around car shows is powered by a thumping V8 and many have the lauded 4-speed manual. Oooohh...ahhh...pssshaa, meh!  Those hot rod upgraded powertrain combos are great if you plan to go vintage racing or like to head to the drag strip, but most classic cars are just putted around town by old guys, so why not get something that'll get good fuel economy and isn't as common as pimples on a teenager.  Like a straight-6 mated to a..errr..2 or 3...let's just say several speed slushbox. Find this 1963 Ford Falcon Convertible offered for $15000 in Port Orchard, WA via craigslist. Tip from FuelTruck.

Join The Rotary Club: 1988 Mazda RX-7 Convertible

The second generation Mazda RX-7 was known as the FC and over 270,000 examples were built in Japan from 1985-1991 for worldwide consumption.  The FC was, of course, powered by a Wankel rotary engine and featured the athletic reflexes matched by few cars in the 1980s. If you can live the eccentricities of the odd spinning thing under the hood, these cars are sublime to drive.  Find this 1988 Mazda RX-7 offered for $2,500 in Burien, WA via craigslist. Tip from FuelTruck.

996 In Blue: 1999 Porsche 911 Convertible

The Porsche 911 is an iconic classic imbued with a finely tuned suspension, classically understated good looks and raucous sounding rear mounted flat-6 engines - a combination that is seldom imitated.  The 996 was a 911 that was faster, more comfortable, and better than the previous generation, but of course the purists and naysayers complained about the changes to watercooling...etc etc. Ironically, for the first time in Porsche history, they were correct...perhaps.  Find this 1999 Porsche 911 996 offered for $14500 in Redwood City, CA via craigslist. Tip from Fuel Truck.

Wassergekühlt: 1990 Porsche 944 S2 Convertible

The Porsche 944 was another chapter in the watercooled front engine Porsche sport coupe saga that started in the late 1970s with the 928...but the 944 is in essence a beefed up replacement for the 924.  The 944 is actually one of the better cars of the 924/944/968 extended family to pick up from a cost/drivability/fun perspective because they have been (mostly) shunned by the hipsters over at Lufthgek...Lufget...Looofgeekcult....Luftwafflehouse...Luftgekühlt...because of the lack of luft in the gekuhlt.  Find this 1990 Porsche 944 S2 Convertible offered for $16000 in Mercer Island, WA via craigslist. Tip from JB1025

Xtra Lively: 1970 Ford XL Convertible

The Ford Galaxie was launched in 1959 as a plus sized top of the line version of the already fullsized Ford Fairlane, but by 1970 it was known simply by the name XL...which didn't stand for Xtra Large but meant Xtra Lively.  This next car is a beast of a classic for that is powered by a 390V8 and has a cool coat of brownz (yeah...brown and bronze) paint and hidden headlamps all offered for a very reasonable price.  Find this 1970 Ford XL Convertible offered for $8900 in Ramona, CA via craigslist.