DALLAS, TX.- When Gary Keller was a little boy, he and his dad bonded over “all the coolest stuff,” Gary says. Like G.I. Joes, packs of Batman and Wacky Packages cards, monster and racecar and sports-moment model kits, Captain Action superhero figures, playsets and puzzles and comic books. The bright stuff. The fun stuff. The scary stuff. The silly stuff. All the stuff.

“I did pretty good when I was a little kid,” says Keller, whose father was a cheerleader for childhood. The longer the Chicagoan talks about his dad, the more he makes it sound like every morning in the Keller household was Christmas morning. “But there was a lot of stuff that was too expensive, too,” the 60-year-old Gary Keller says now, “things we couldn’t 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. That’s how Keller amassed what came to be known as The 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,” Keller says. “I don’t 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: Browse The Windy City Collection: Action Figures & Toys Signature® Auction, which takes place Nov. 20-21 and contains more than 500 pieces from Keller’s sprawling collection. It’s 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, including the highly sought-after Batman and Justice League of America Play Set from 1966, but original paintings that became G.I. Joe and Captain America model packages, Six Million Dollarand Time Tunnelcoloring book covers and Garbage Pail Kids, Wacky Packages and Caped Crusader trading cards.

The auction is now open for bidding, and among its myriad centerpieces is the 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 Hasbro’s 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 artwork is the earliest and only known surviving piece dating to G.I. Joe’s debut, and it’s 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,” Keller says. “Then again, people didn’t know I had this, either.”

This event marks the first time the work has been available at auction.

Petrucci’s 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, painterly 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 today’s real American hero. Stivers, a Navy veteran and fine artist whose subjects spanned the Civil War and the Buffalo Soldiers to World War II, defined the action figure as much as G.I. Joe’s new grip.

Keller offers five of Stivers’ works in the auction, beginning with two from 1972: the original art for the G.I. Joe Adventure Team Missile Recovery packaging and the painting used to package G.I. Joe’s Recovery of the Lost Mummy Adventure. From 1973 hails the Dangerous Mission Action Outfit artwork; from ’75 comes the Adventure Team Chest Winch package painting.

But perhaps his most famous work for Hasbro hails from 1973: the painting for the package containing the G.I. Joe Adventure Team Sea Adventurer with Kung Fu Grip. Before then, Joe couldn’t hold jack or squat. But King Fu Grip was a game-changer for kids — even if it just consisted of soft rubber used to make the hands, which eventually wore out. But it doesn’t matter whether you played with it 50 years or five days ago; Stivers’ artwork, featuring the man with the “like-like hair and beard” extending that massive left mitt, is a definitive 1970s memory.

“To me, those were always art pieces,” Keller says, “no different than comic art and card art.”

And there’s 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 his Mars Attacks cards in the early 1960s. In 1966, just as Batman was setting up camp on ABC, Topps introduced its illustrated cards (six sets in ’66 alone!), which have proved among The Hobby’s most enduring non-sports cards, with Batman’s “rookie” card realizing a record $45,000 at Heritage this summer. As Topps noted in July, “The cards from Saunders have a timeless comic-book feel.”

This auction features two of Saunders’ original paintings from Topps’ 1966 Batman series: “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: 1967’s Wacky 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 the Wackys for a decade as they evolved from sticker cards to posters; Keller includes in this auction Saunders’ original art for 1974’s Hipton “Hippy” Tea Bags poster, which promised to give you “the energy to loaf, hitch hike and avoid work,” far out.

“Wacky Packages were something I remember from second grade when my friends and I would walk two blocks to the drug store to buy the first series,” Keller says. “It was huge. 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 he’s downsized in recent years — and because, like all good collectors, he knows he’s just a temporary caretaker. It’s 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.”