Pebble's best: a judge's perspective

A legendary machine if there ever was one, this is the Mercedes-Benz 300SLR that famed British sportsman Stirling Moss piloted to victory in the 1955 Mille Miglia, an Italian road race that ran from Brescia to Rome. Along with navigator Denis Jenkinson, Moss finished the 1,000-mile journey in 10 hours, 7 minutes and 48 seconds, at an average speed of 97.96 mph — a feat that was never repeated. "Mechanically, with its 8-cylinder, single-overhead-cam engine and magnesium body, the vehicle was really ahead of its time," Gross says. "Stylistically, it still looks better than most exotics." Little-known fact: The number 722 was actually the time the car started the race, at 7:22 a.m.

View Pictures:  Monterey Motorsports Reunion

The Ferrari 250 GT is undeniably the sexiest car ever built. At least in this journalist's eyes, there has never been a machine in which form and function are so in tune. Only 39 GTs were ever created, and they dominated the international racing scene in the 1960s. "This one is actually the 250 GTO prototype," Gross says. "It's the first Ferrari to bring together the 250 SWB chassis — somewhat modified for racing — with a race-spec three-liter V12. And just look at it. Wow!"

View Slideshow:  The Ferrari GTO

In 1931, the Swallow Sidecar Co. of Coventry, England, combined a Standard Motor Co. 16-horsepower inline-6 engine with a low-slung, slightly modified chassis, also from Standard, to create its first true sports car, the SS1. At the time, Swallow cars were considered sporty-looking but problematic; performance did not live up to the looks. "But this car was different," Gross says. "Not only did it perform well, with a top speed of about 75 mph, but it was stylish and relatively affordable. It is also considered to be William Lyons' first total design." Just over 4,200 SS1s were made. The SS Co. changed its name to Jaguar after World War II, for obvious reasons.

View Slideshow:  Run, Big Cat, Run

Parisian coach builders Figoni & Falaschi were masters at shaping vehicles that were both aerodynamic and evocative. The dramatic teardrop design of this F&F creation gives the illusion of motion even at a standstill. The first T150-SS was introduced to the world at the 1937 Paris Auto Salon. This one followed suit in New York the same year. Originally intended for racing, it features a 3-carburetor, 4-liter inline 6-cylinder motor with a hemi head. Since these were hand-built bodies, each vehicle has different and unique characteristics. "No two T150-SS's are the same," Gross says. "No side is the same. The car doesn't have a single straight line. And it is exquisite from any angle."

Watch Video:  2011 Pebble Beach Highlights

Launched at the 1928 New York Auto Show, the Duesenberg Model J was an instant sensation. Powerful, well built, fast and elegant, it was then the pinnacle of American automotive design. This particular model is outfitted with a one-of-a-kind body built by Pasadena, Calif.-based Murphy Designs. Over the years, Murphy was responsible for some of the most desirable and elegant Duesenbergs. It also bears the firm's first disappearing-top convertible. "It's the prototype for a Murphy roadster," Gross says. "And it's a real performer, with a 420-cubic-inch, 325-horsepower supercharged engine under the hood."

View Slideshow:  Going Once, Going Twice — Sold!

This is one of only four Runabouts ever built. While none were exactly alike, they were all built on Packard's short-wheelbase 1108 chassis and powered by a 160-horsepower V12 engine. This exquisite example also features a single Stromberg carburetor and an automatic cold start feature, which was unique for the time. The dramatic streamlined body was designed by LeBaron but built by Packard's custom body shop. "Those pontoon front fenders and skirted rear wheels were considered quite racy back in the day," Gross says. Indeed.

Read Blog:  She's 101, Her Packard Is Only 81

This is truly one of the world's finest automobiles. From the aggressive front fenders to the long, tapered rear treatment, its lines are hypnotic; skirted rear fenders add to the feeling of grace in motion. It is one of four 57Cs built that features the Gangloff Aravis body. The sleek design is enhanced by the amazing green two-tone color scheme. "It's sporty and elegant," Gross says. The car is powered by a supercharged 3.3-liter 8-cylinder engine, which puts out about 160 horsepower.

View Pictures:  2011 Motoring Classic

The Model 40 Special Speedster was unlike anything Ford had ever built. It was actually Edsel Ford's personal vehicle. He asked the automaker's chief designer, Bob Gregorie, to design and supervise the construction of a personal sports car similar to those he'd seen while on a trip to Europe. Since Ford's death in 1943, the vehicle has changed hands many times and gone through numerous modifications. But RM Auto Restoration in Ontario, Canada, spent the last year restoring the Model 40 back to its original condition. "And they did an amazing job," Gross says. "This is a true one-of-a-kind masterpiece, with innovative styling and stellar performance."

View Pictures:  Pebble Beach Tour d'Elegance 2011

For nearly two decades, New York-based writer and editor Chuck Tannert has covered everything from automobiles to gadgets to travel. Before joining the MSN Autos team, Tannert served as senior automotive editor at Cargo and Popular Mechanics, and his work has appeared in many outlets, including Men's Fitness, Men's Journal, Penthouse, Popular Science and Wired.