The Chevrolet SSR is one weird truck. It's got two seats and a bed, sure, but it also has a retractable hardtop and, for the 2005 model year, a 390-horsepower LS2 V8 engine borrowed from the Corvette. It's not the most utilitarian truck money can buy, but few pickups can haul away looks like this one.
With an automatic transmission and 132,000 miles on the odometer, expect to spend right about $20,000 on a clean SSR. I'm not going to talk about the interior, because, like most pre-bankruptcy GM vehicles, the SSR's interior is a sad menagerie of hard plastic and fake shiny bits.
Avoid 2003-2004 models fitted with the 5.3-liter Vortec 5300 engine if you want performance worthy of the SSR's attention-grabbing looks.
2011 Honda Ridgeline RTS -- Jon Wong, road test editor
The first-generation Honda Ridgeline debuted innovative features like a two-way tailgate, 5-foot-long composite bed and 8.5 cubic-feet in-bed trunk to offer heaps of pickup-truck flexibility, while an independent front and rear suspension delivered car-like ride comfort.
With its 250-horsepower, 3.5-liter V6, and standard all-wheel drive, the Ridgeline has a max tow rating of 5,000 pounds. Nobody will mistake its pulling prowess for that of a full-size truck, but for most people, it's all the pickup they'll ever need.
2006 Dodge Ram SRT-10 -- Chris Paukert, managing editor
If I told you that you could get a rear-wheel-drive, V-10-powered sports car with 500 horsepower and 525 pound-feet of torque for $20,000, wouldn't your interest be piqued? Now, what if I told you that same ride could haul around your family and all of their clutter while towing up to 8,150 pounds of whatever extreme sports gear you're into?
That's the winning premise of Dodge's certifiably insane Ram SRT-10, a short-lived Viper-powered SRT muscle truck.
Available in both standard two-door and Quad Cab formats, the SRT-10 is a very entertaining and surprisingly useful proposition, but its prodigious thirst means it's probably not well-suited to daily driving. EPA figures for the six-speed manual are 9 mpg city and 14 highway, and the optional four-speed automatic is even more reprehensible at 8/11.
But if you're considering this sport truck, you're probably more interested its giggle-inducing 5-second 0-60-mph sprints and 150-mph top whack, not its Greenpeace credentials, right? If nothing else, given the SRT-10's performance and rarity (fewer than 10,000 were built between 2004 and 2006), it's likely to appreciate as a collector vehicle down the road.
2007 Cadillac Escalade EXT -- Wayne Cunningham, managing editor
If you want a Cowboy Cadillac, a term for any high-trim pickup truck, why not get one with an actual Cadillac badge on the grille? General Motors' luxury division offered the EXT version of the Escalade, with a short, 5-foot bed, from 2002 to 2013. The Escalade EXT had a twin in the Chevrolet Avalanche, but featured upscale interior elements along with more refined suspension tuning and all-wheel drive instead of four-wheel drive.
The 2007 Escalade EXT represents a generational update over the 2006 model year, following the standard Escalade SUV. As such, it gets a 6.2-liter V8 making 403 horsepower, a 58-horsepower increase over the 2006 model year.
The Escalade EXT was sometimes referred to as an SUT, or Sport Utility Truck. It had two full seating rows up front, like its sibling SUV, but the rear made way for a pickup bed. Although a short bed, Cadillac extended its utility with the "midgate" shown here, a bottom-hinged door that let longer items run into the cab.
Although a 2007 Escalade EXT blows past our NADA price limit at $22,425, it's a Cadillac, so it's a step above your typical pickup. Besides, if you peruse the online classifieds in your area, my research suggests you'll find one available for under $20K. Still can't swing one? Because of the generational update, the 2006 model year can be had for substantially less, at an NADA-estimated $17,500 fully loaded.
2011 Toyota Tundra -- Antuan Goodwin, Associate Editor
Come for the 381-horsepower, 5.7-liter gasoline V8; stay for the 9,200-pound towing capacity and the Toyota Tundra's reliability reputation. This full-size pickup's 401 pound-feet of torque gets sent to an available four-wheel-drive system via a six-speed automatic transmission.
Tucked inside the Tundra's handsome exterior, there's well-made (if a bit plasticky) cabin.
The second-generation Tundra fits nicely into our price range, but there are some things you should look for. 2007 to 2009 models feature an older 4.7-liter V8 that makes less power, but these less expensive years free up space in the budget for a more flexible double-cab body. 2010 or newer examples with the newer 4.6-liter engine or, even better, that beefy 5.7-liter can only really fit into the budget with the less desirable, but still viable, single-cab configuration.
2004 Porsche Boxster -- Brian Cooley, editor at large
My taste in trucks runs to XLTs and Lincoln Blackwoods, so fit me for rhinestone work boots, I guess. The F-150 King Ranch variant is named for the largest ranch in Texas and epitomizes Texas establishment: George W. Bush drove a white 2009.
Our $20K spend will get you a 2WD version in fine condition, though you'd need a couple grand more for 4WD. 2009 was the start of a new generation of F-150 that sported a tougher Super Duty look up front, dipped window sills on the front doors and 3,300-pound payload rating.
Don't sweat the navigation option on one of these, it was just too long ago for it to be very satisfying by today's standards. 2009 seems to be a very problem-free first year for the 12th generation F1-50 with very little to note in the way of recalls, TSBs or other teething bugs.
2008 Toyota Tacoma TRD Off-Road -- Emme Hall, road test editor
It's a testament to Toyota's reputation and sterling resale value that you have to go all the way back to 2008 to get a Tacoma TRD Off-Road model that comes in at $20,000. As an off-road geek, the TRD package is an absolute must for me. A locking rear differential and Bilstein shocks are sure to help out in the dirt, and the smaller 16-inch alloy wheels mean there is room for bigger off-road tires.
The Double Cab is worth the extra price just for the convenience of being able to lock up your expensive desert gear and the 4.0L V6 knocks out 236 horsepower and 266 pound-feet of torque. With the towing package the Taco can haul 6,500 pounds of weekend toys.
Just keep in mind that someone who bought a brand-new TRD-equipped Tacoma more than likely banged it around in the rough stuff, so check the skid plates and suspension components for wear. In particular, look for any cracks or dents in the frame, which would indicate some serious dirt hooning.