Nike Moon Shoe Waffle Racer

It's hard to overstate the importance of Nike's original "Moon Shoe". Famously born when Nike co-founder Bill Bowerman poured rubber into his wife's waffle iron, the shoe offered both better grip and better comfort than other running shoes of the time, giving the fledgling company its first real innovation. The pair seen here was hand-cobbled by early Nike employee Geoff Hollister, and was one of just 12 pairs created for runners at the 1972 Olympic Trials. Made from white nylon with black Swooshes, they're the only pair known to exist in unused, deadstock condition, and are being offered by Stadium Goods and Sotheby's.

Marlon Brando's Apocalypse Now Rolex GMT-Master Watch

Seen on the wrist of Colonel Kurtz in Francis Ford Coppola's masterpiece Apocalypse Now, this Rolex GMT-Master is far more than a simple movie prop. The watch, worn by Marlon Brando's iconic character on screen, remained in the actor's possession until 1995, when it was gifted to his daughter. At some point Brando himself engraved the back with "M. Brando", leaving no doubt as to where the watch came from. The watch will be offered by Brando's daughter Petra and her husband Russel at Phillips in New York on December 10.

Photos: Phillips / Mary Ellen Mark

Field-Worn 1968 Omega Seamaster 300 Watch

Found in a briefcase after 40+ years, this Field-Worn 1968 Omega Seamaster Watch is both an outstanding vintage timepiece and an artifact of an American hero. Owned by Legion of Merit and Bronze Star recipient Lieutenant Colonel George Aikman Finter, the watch is in an unpolished state yet is in remarkably good condition. LTC Finter served in post-war Germany, did a stint as an intelligence officer in Chile during a time we weren't supposed to be there — potentially indicating he was a spy — and did four tours in Vietnam before being killed in action during a recon mission in 1970. The watch will be sold alongside a number of records detailing Finter's military career, including IDs, passports, licenses, photos, his report of casualty, Bronze Star Citation, and hand-signed letters of condolences from then-President Richard Nixon and General Westmoreland.

Jack Nicklaus' Rolex Day-Date Watch

Jack Nicklaus had already won six major championships by the time Rolex gifted him this Reference 1803 gold Day-Date watch. Which means it was on his wrist for a staggering 12 more. The first watch Nicklaus ever owned — Gary Player suggested the model to him — it has been witness to more golf history than perhaps any other timepiece. The Golden Bear's daily wearer for 50 years, he's now putting it up for auction, with all of the proceeds going to the Nicklaus Children's Health Care Foundation. The auction will take place in New York on December 10; prior to that, it will be on display at various places around the world, including the Jack Nicklaus Museum in Columbus, Ohio, and the US Open at Pebble Beach.

Photos: Nicklaus Companies / Phillips

1916 Babe Ruth Rookie Card

Long overshadowed by the legendary T206 Honus Wagner and 1952 Topps Mickey Mantle rookie, Babe Ruth's 1916 M101-4 Sporting News rookie card is finally receiving the attention it deserves. This particular one is a fine example, rated a Good-Very Good 2.5 by Beckett Grading Services. Recently discovered inside an antique piano as it was moved, it has a blank back, shows the Bambino as a lefty pitcher for the Red Sox, and is ready for display as the crown jewel of any memorabilia collection.

Ayrton Senna's Gold Rolex Daytona Watch

Given by legendary racer Ayrton Senna to his mentor Angelo Parrilla, this Rolex Cosmograph Daytona in 18K yellow gold is a rare watch with a historic pedigree. Parrilla is credited with "discovering" Senna and bringing him to Italy when he was just 18, putting him on the road to greatness. This close relationship is evidenced on the watch's gold caseback, which reads "A Angelo da Ayrton 1978", or "To Angelo from Ayrton". The watch itself is also notable as a reference 16528, the earliest of Rolex's automatic gold chronograph Daytonas, and has both a rare floating dial and a desirable Mark 1 bezel. It will be accompanied by an autographed picture of Ayrton Senna, an autographed helmet faceguard, a letter from Angelo Parrilla confirming the watch was gifted to him, photographs, and the original box, service guarantee, pouch, and product literature.

1943 Bronze Lincoln Cent

Copper and bronze were in short supply during World War II, which is why all pennies from 1943 are made from zinc-coated steel, instead. Almost all, anyway. This 1943 Bronze Lincoln Cent is one of just 10-15 surviving examples of pennies made from bronze planchets left over from 1942. They were fed into the coin press along with the steel planchets meant for 1943 production, and the resulting cent pieces subsequently slipped into circulation. This particular example was given to a high-school student in his cafeteria change in 1947 and was kept by the student until recently, when it went up for auction and sold for $204,000.

Fair Weigh Golf Scale

Built by the Colonial Scale Company around 1930, this Fair Weigh Golf Scale is a rare piece of Americana. One of only three known to still exist, it incorporated a complex golf game in the bottom. In the game, the user swings a small golf club with the turn of a knob, in hopes of sending their penny over the lake, past the obstacles, and into the hole. Fail, and the penny fell into the lake and thus the operator's cash box. Measuring six feet tall, it's in exceptional condition, and would be a highlight piece in any den, clubhouse, or collection.

Neil Armstrong Boot Prototype

Made by the International Latex Corporation (ILC) in Dover, Delaware, this boot was originally built to support the Apollo 11 mission. It has the light blue silicon tread, aluminized Mylar insulation layers, and gold-tone Kapton tape and liner of the boots used on the moon. However, it lacks the outer Beta cloth, Chromel-R fabrics, and some of the snaps and straps of the mission-ready pairs, meaning this pair was likely rejected for some reason. That same fact also means they are far better preserved than a pair that saw actual use, with the "Armstrong" name tag still intact.

John Mollo's Star Wars Sketchbooks

Though Ralph McQuarrie came up with the original Star Wars paintings, John Mollo turned those dreams into a reality. Mollo was tasked with providing detail for every costume for the entire cast of Star Wars: A New Hope and The Empire Strikes Back — a massive assignment that later won him an Academy Award. Mollo passed away last year, and his family is offering up for auction some of his original sketchbooks that provide personal insight into the creative process of a legend. Both custom bound volumes contain production diary entries, meeting notes, and working sketches of many characters from the original trilogy as well as other projects Mollo worked on during this time frame. The books are expected to fetch well over $100,000 each and provide a unique opportunity to own a part of cinematic history.

Hunter S. Thompson Letter Archive

Made up of 182 letters, including handwritten, typed, signed, telegrams, and postcards, as well as three drawings, this Hunter S. Thompson Letter Archive is a treasure trove of writing from the storied author. The vast majority of the letters, dated from 1955 to 1974, are from Thompson to childhood Paul Semonin, and show the evolution of his signature Gonzo style, as well as recounting his time in Big Sur, the writing of The Rum Diary, and his time with — and beating by — the Hell's Angels that inspired the book of the same name. Of historical importance is a famous letter written the day of JFK's assassination, which was only partially published, along with 24 of the other letters, in The Proud Highway: The Saga of a Desperate Southern Gentleman 1955-1967. As a whole, the lot represents a one-of-a-kind look into the inner workings of one of the last century's greatest authors.

License To Kill Rolex Submariner Watch

Worn by Timothy Dalton's stunt double during the filming of License To Kill, this Rolex Submariner Watch is a wearable piece of Bond memorabilia. Notably, the watch was featured during a car chase scene in Mexico, during which 007 takes a tanker truck up onto its left-side wheels to dodge an incoming missile. The lot includes photos of the cast and crew on location in Mexico, paperwork from Rolex, a book about the making of the film, and a certificate of authenticity from EON Productions.

Soviet Spy Cameras

Digital technology has rendered film (mostly) obsolete, and modern surveillance has done the same to old-fashioned espionage. Thus this auction of Soviet-era spy cameras is a treasure trove of outdated-yet-timeless hardware. Ranging in age from 75 to 30 years old, most of the cameras still work, with examples including a gum pack-sized Minox Riga, a camera hidden in a dinner jacket, a camera disguised as an umbrella, and even a camera hidden inside... a camera. The auction will be held on July 12 and run by Aston's of England.