Hasbro's special-edition Theodore Roosevelt G.I. Joe figure from 1999 doesn't have kung-fu grip or an arsenal of tank-busting accessories to go into battle with. Instead, his signature toothy grin, glasses, and Rough Rider uniform from the Spanish-American War are all meticulously recreated on a figure that's better suited for display than play. Though the toy doesn't quite fit in with the likes of Duke, Snake Eyes, and Cobra Commander from G.I. Joe's '80s heyday, it turns out that the rancher-turned-soldier-turned-president was a perfect fit for a toy line that was ready to embrace reality again.

The "Real American Hero" Gets Canceled

At its peak in the 1980s, Hasbro estimated that two out of every three boys between the ages of 5 and 11 owned a G.I. Joe action figure. But by the mid-'90s, the once-famous "Real American Hero" line of 3.75-inch figures that had been the brand's foundation was discontinued in the face of slowing sales.

"They were losing kids to Teenage Mutant Ninja Turtles and other new brands," Derryl DePriest, the former vice president of global brand management and author of the books The Collectible GI Joe and Star Wars: The Vintage Collection Archive Edition, tells Mental Floss in an email.

A changing toy market and stiff competition were partly to blame for these cancellations, but a key shift came in 1991, when Hasbro bought rival toy maker Kenner, which soon assumed control of both G.I. Joe and Transformers.

"Kenner was a boy's toy powerhouse, having held the license to Star Wars, Batman, [and] Ghostbusters,” DePriest says. "[They] had a hot hand, and naturally with the change of management, they wanted to put their own stamp on it."

Though the company tried new initiatives in '95 and '96—like the 5-inch "G.I. Joe Extreme" line, which DePriest called "a disaster"—they were usually discontinued within a year. Joe was still a moneymaker, but it was clear that its popularity was sagging, especially now that it was under the same roof as the Star Wars juggernaut. Turns out, to evolve, the brand just needed to go back to its roots.

G.I. Joe Goes Retro

When G.I. Joe first launched in 1964, it entered the market as a series of 12-inch figures, complete with cloth outfits, 19 points of articulation, and plenty of accessories. By the ‘90s, fans of those originals were now adults with disposable income looking to recapture a bit of their youth and share the 12-inch version of Joe with their own kids. Hasbro was starting to take notice.

"The team at Hasbro was aware of the nostalgic interest in [12-inch G.I. Joes] beginning in the late ‘80s," DePriest says. "They first tested the waters with a 12-inch product at the request of Target in 1991, with a version of Duke with sound effects marketed under the ‘Hall of Fame’ collection."

That initial 1991 attempt didn’t scratch the nostalgia itch—the figures were 12 inches like the originals, but they were overly bulky and lacked the articulation of their ‘60s counterparts. So the team tried again in the mid-‘90s, but this time they fully embraced the retro look and feel for a new line called the “Classic Collection,” which launched in 1996.

The toned-down body design was far less chunky and restrictive, meaning the team was no longer shackled to only producing toys based on squared-jawed heroes with barrel chests and sleeve-shredding biceps. The new line stuck close to its vintage bread and butter: U.S. Army tank commanders, helicopter pilots, and Marine snipers were some of the early offerings.

But the team decided to take advantage of the newfound flexibility by introducing figures based on real-world war heroes, presidents, and other important historical figures, too. It was something that appealed both to older collectors and the history buffs at Hasbro.

"At one point, we had George Washington, we had done a General Patton, General Eisenhower, Colin Powell. And then we had also done Congressional Medal of Honor recipients; the first one being Francis Currey," Kurt Groen, the former designer behind the 12-inch line at Hasbro, tell Mental Floss.

The line soon found an audience, and, of course, more figures (and more media attention) followed.

"Some of the real-world personalities that got the most attention included a WWII tribute to John F. Kennedy, as well as astronaut Buzz Aldrin and the voice of the common soldier, Ernie Pyle," DePriest said. There was such demand that even offbeat choices like Bob Hope and Ted Williams got the green light.

Teddy Roosevelt: The Perfect G.I. Joe

When asked why he chose Roosevelt for the 1999 line, Groen's answer was simple: "I wanted to do him." That's the type of carte blanche he was given by Hasbro on the 12-inch line. Groen also knew, as an admirer of Roosevelt, that the colorful hero of the Spanish-American War embodied the spirit the company was looking for.

"Teddy Roosevelt was a natural fit," Groen says. "He's bigger than life. So, that was an easy pick in the whole process."

The moment the design process started, Groen knew that the Roosevelt figure couldn't be just TR as president ready to sit down for a meeting at the White House. G.I. Joes need to be ready for war—so Roosevelt needed to be a Rough Rider again.

"[Before] he did the Rough Riders, he would dress up and play the part or go out West and kind of live the Remington life," Groen says. "And then after he did the Rough Riders, he was focused fully on the political side of life. So there was no other place to go then."

Picking the outfit was the easy part—next, Groen needed to pay close attention to every detail if this figure was going to work.

"[I] contacted a couple of parks, a couple historians. And then I've got books [on his uniforms] like you wouldn't believe," Groen said about the process of nailing down the design details. Every inch of the sculpt was important to get right, but some of the details that Groen still remembers more than 20 years later are Roosevelt's smile, which practically beams off the figure's head; the distinct shape of his mustache; and his glasses.

Hasbro's Theodore Roosevelt G.I. Joe figure was based on his Rough Rider uniform worn during the Spanish-American War. Wikimedia Commons // Public Domain

The research paid off. Roosevelt’s entire ensemble from the war is represented on the figure—highlighted by the slouch hat, Colt revolver, and polka-dotted bandana that can be seen in so many paintings and photographs from the time.

"If you remember the picture of him standing with the troops on top of San Juan Hill—that's where the big inspiration came from for the figure," Groen said.

The figure would officially hit store shelves in 1999—and 20 years later, many can still be found untouched and in their original box for anywhere from $60-$80 online.

The fact that people are still buying Roosevelt and other "Classic Collection" figures in mint condition today was all by design. As Groen said, "We weren't really designing toys." Though Groen was concerned with playability during the design phase, figures like these were made for collectors who likely never remove them from their window-box packaging.

Whether or not Groen and the team at Hasbro ever imagined kids pitting Teddy Roosevelt against Duke, Snake Eyes, or Cobra Commander is anyone’s guess. But in terms of fitting seamlessly into the world of G.I. Joe, it's hard to argue against TR.

"If you look at him and the way he held himself, he was a perfect character,” Groen said. “I mean, when you talk about characters of history, he is a character of history."

Mental Floss has a new podcast with iHeartRadio called History Vs., about how your favorite historical figures faced off against their greatest foes. Our first season is all about President Theodore Roosevelt. Subscribe on Apple Podcasts here, and for more TR content, visit the History Vs. site.