When Gary Keller was a little boy, he and his dad bonded over all the coolest stuff, recalls Keller. Like G.I. Joes, packs of Batman and Wacky Packages cards,monster and race cars and sports-moment model kits,Captain Action superhero figures, play sets, puzzles, and comic books. The bright stuff. The fun stuff. The scary stuff. The silly stuff. All the stuff. But there was a lot of stuff that was too expensive, too, the 60-year-old Gary Keller says now, things we couldnt afford.That childhood problem was easily solved by adulthood, a successful business, trade magazines filled with ads for entire toy collections and, later, a start-up called eBay that made it so easy to buy everything missing from his shelves. Thats how Keller amassed what came to be known asThe Windy City Collection, an enviable assemblage filled with vintage action figures, sealed toys and unassembled puzzles, and the original artwork that once graced the packages in which those fond memories were sold. My collection makes me feel good, said Keller. I dont know how else to explain it. I have pieces all over my place. Everywhere. You can stand in my living room and see 20 pieces. I become a kid when I look at them. The joy is contagious. Titled BrowseThe Windy City Collection: Action Figures & Toys Signature Auction, the event will take place Wednesday and Thursday, Nov. 20 and 21, and contains more than 500 pieces from Kellers sprawling collection. Its an ear-to-ear grin, an event awash in warm memories, an endless feast of nostalgia that includes among its offerings not just those sealed (and often graded) toys, includingthe highly sought-after Batman and Justice League of America play set from 1966, but original paintings that became G.I. Joe andCaptain America modelpackages,Six Million DollarandTime Tunnelcoloring book covers andGarbage Pail Kids, Wacky Packages and Caped Crusader trading cards. The auction is now open for bidding, and among its myriad centerpieces isthe original box artwork for the G.I Joe Action Sailor, which stormed shelves in 1964. This piece is by Sam Petrucci, the Ritz Carlton bellhop-turned-Naval radio operator who, by the mid-1960s, spent five years as Hasbros G.I. Joe artist, an oft-uncredited maker of memories who gets his due in this auction. Petrucci was a hot commodity, illustrating board games and toy packages for Mr. Potato Head, The Banana Splits and Superman. During his tenure at Hasbro, Petrucci not only painted the artwork for all four of the original G.I. Joe boxes but also designed the logo. The Action Sailor original artwork is the earliest and only known surviving piece dating to G.I. Joes debut, and its a quintessential work, the recon diver with a knife in one hand and dynamite in the other. This original box art is among the scant survivors from the original G.I. Joe line that we know of, according to Keller. Then again, people didnt know I had this, either. This event marks the first time the work has been available at auction. Petruccis painting is joined by a handful made by the man who replaced him in the 1970s, Don Stivers, best known, according to The Joe Report, for his aggressive style (and) bright, colorful palette. Stivers was also tasked with giving Joe a makeover amid the war in Vietnam, from enlisted man to Adventure Team member, from the soldier of yesterday to todays real American hero. Stivers, a Navy veteran and fine artist whose subjects spanned the Civil War and the Buffalo Soldiers to WWII, defined the action figure as much as G.I. Joes new grip. Keller offers five of Stivers original works in the auction, beginning with two from 1972,the original art for the G.I. Joe Adventure Team Missile Recovery packagingandthe painting used to package G.I. Joes Recovery of the Lost Mummy Adventure. From 1973 hails theDangerous Mission Action Outfit artwork; from 75 comes theAdventure Team Chest Winch package painting. And theres plenty of card art here, too, most famously those painted by Norman Saunders, the pulp magazine cover artist hired by Topps in the late 1950s to paint baseball players and rose to prominence (and infamy) with hisMars Attackscards in the early 1960s. In 1966, just asBatmanwas setting up camp on ABC, Topps introduced its illustrated cards (six sets in 66 alone), which have proved among the hobbys most enduring non-sports cards, with Batmans rookie card realizing a record $45,000 recently at Heritage. This auction features two of Saunders original paintings from Topps 1966Batmanseries: Batman Wins a Prize and Batman Bucks Badman, the latter of which is so rare that PSA has only graded seven cards. These paintings are the ultimate one-of-ones. Saunders most popular project for Topps came a year after he left the Batcave: 1967sWacky Packages, which parodied everyday things, in this case, Alcohol-Seltzer, a painting made for a die-cut card that became among the long-running series most popular. Saunders stuck with theWackys for a decade as they evolved from sticker cards to posters; Keller includes in this auctionSaunders original art for 1974s Hipton Hippy Tea Bags poster. Wacky Packageswere something I remember from second grade when my friends and I would walk two blocks to the drug store to buy the first series, said Keller. It washuge. The first series swept the nation because they were considered too gross and obnoxious at the time. No one ever put something like that out. And when the opportunity arose to own original artworks, I had to have them, like everything else in my collection. Keller is parting with only some of his extraordinary assemblage, and only because hes downsized in recent years and because, like all good collectors, he knows hes just a temporary caretaker. Its time for someone else to love these pieces as much as he has for as long as he has. Whenever I look at these things, they release endorphins, Keller says. And I just start smiling. To learn more, visit www.HA.com.