I imagined what it would be like if I'd just won big on "Jeopardy!" and had money to burn on some dream vehicles. Here's how I would fill a three-car garage. Even though all are off-road capable, each one has a very different personality and serves a different purpose. When possible, I went to each manufacturer's Web site and built them exactly as I'd want them—now all I have to do is hit the Daily Double.
1) 2008 Grand Cherokee Diesel
I've been a fan of the newest generation of Grand Cherokees since they came out a few years ago. Not only is this the first gen of Grand Cherokee that offers a turbodiesel, but it has the best interior to date, with enough room for my friends, family, and gear (I don't need three rows). Plus, the Grand Cherokee's always provided a great combination of off-road capability and on-road comfort. When I built my ideal Grand Cherokee on Jeep's Web site, I chose a Limited 4x4 with Steel Blue Metallic paint. (The actual color looks better than it does here.) And, as you might expect, I chose the 3.0-liter, 215-horse turbodiesel with 376 pound-feet of torque. By the time I'd finished checking the options boxes, my Jeep cost $40,940. That's a little steep, but I did want nav, Sirius, and several other cabin amenities. However, it's good to know that the turbodiesel is also available as an option on the less-expensive Laredo.

2) Toyota Land Cruiser
For the second vehicle on my list, I went to Toyota's Web site and built my ultimate Land Cruiser. This is one of the few remaining true sport/utilities on the market: body-on-frame, full-size, solid rear axle. The Land Cruiser is one of the most unstoppable vehicles money can buy—as long as the trail you're on is wide enough. And, for 2008, the TLC can tow 8500 pounds. This SUV does things it shouldn't be able to do: It's incredibly comfortable on the highway, fiercely capable off-road, and reaches 60 mph in less than 6.5 seconds. Unfortunately, it's really, really expensive. I chose an Amazon Green Metallic model with Sand Beige leather; there aren't many other choices to make. It comes with the Tundra's awesome 5.7-liter V-8 (381 horsepower, 401 pound-feet) and six-speed automatic, plus Crawl Control, which may be one of the best innovations from 2008. I added XM radio, an emergency assistance kit, and a seven-pin to four-pin adapter, bringing the bottom line to $71,662. The only thing that could possibly make this SUV any better is a diesel option.

3) 2010 Ford F-150 Diesel
Yes, I realize the third vehicle on my list hasn't gone on sale yet. I'm also aware that even after it is available and I do finally get to drive it, I'll have to wait about another year before the diesel version comes. But this is my dream list of vehicles that I would buy, and the diesel F-150 is on there. I can't price it out yet and I don't even know how much it will tow, but I want a four-wheel-drive SuperCab diesel with the 6.5-foot bed, preferably with the FX4 or Lariat trim package (if the diesel comes with either of those). And I'd get it in black, with tan leather interior. I know this combination will end up costing $35,000-$40,000, but this truck could potentially be best in class for towing and payload capacity, and it has the nicest cabin offered in any half-ton.