I know what you are thinking -- this is all the money with a large gratuity for a Triumph TR8. The wedge shaped thing that isn't quite a classic, and should be well depreciated. However, you might be surprised at the condition of today's wedge salad and rethink your scoffing at the price. Find this 1980 Triumph TR8 offered for $10,999 in Polson, MT via craigslist. Tip from Zach. 
The B5 generation Passat was launched in the 1997 model year with a product that looked/drove/smelled a lot more like an Audi than the previous generation Passat. In 2001 Volkswagen introduced the B5.5, a cosmetically refreshed version of the platform that added more chrome trim (inside and out) some fancy taillights and a unique W8 engine option that could have been...if you were lucky...mated to a 6-speed manual. Find this 2004 Volkswagen Passat W8 4Motion offered for $7325 in Denver, CO via craigslist. Tip from Joel.
The original (SA or FB) generation Mazda RX-7 is a perfect modern classic for the budget car shopper. Prices are about as low as they will ever go and should be on the way up. If you find a nice one, own/drive it for a few years, you might not lose a dime on it, even if you budget for a minor engine rebuild every 75k miles. But don't come crying to me if it blows up and prices drop to scrap parts level because what do I know, I'm just some guy with a high speed internet connection and a soapbox. Find this 1984 Mazda RX-7 offered for $3,800 in Los Angeles, CA via craigslist. Tip from FabianW.
The BMW 2002 was the high end of the BMW Neue Klasse (new class) platform, equipped with 2 liter inline-4 and is a regular on the Daily Turismo because they are fantastic to drive, useable and inexpensive today. The nice ones are starting to command some premium prices and the 2002 Tii featured in Jan was allegedly sold to Billie Joe Armstrong of the band Green Day, we're sure he'll have the time of his life with it. Get this 1975 BMW 2002 single owner survivor currently bidding on ebay for $1,951 reserve-not-met with 6 days to go, located in Mission Hills, CA before it is picked up by another celebrity rock star. (Car submitted by regular DT seller/commenter Tamas; Oprah85 on ebay).
The E36 BMW M3 was sold from 1995-1999 with a sweet sounding inline 6, a 5 speed shift-it-yourself-transmission and standard limited slip differential. The coupe version is far more common and most have been pimped out or crashed by Instagramming teenagers, but the sedan version has room for your kids and qualifies as a sleeper. This 1998 BMW E36 M3 sedan is for sale by the original owner in Fullerton, CA for $7500 asking via craigslist.