Four years ago, Ryan Red Corn was a carpenter living on an American Indian reserve in Pawhuska, Okla. Angered by George W. Bush's re-election in November 2004, he designed a T-shirt depicting the president as the point in a large question mark over the phrase "Manifest Density." He ordered a minimum batch from a local printer and put the shirts online. They sold so well that Red Corn, 27, now runs his own printing press with two full-time employees and a 3,000-square-foot warehouse, turning out over 40 designs for Urban Outfitters and other national retailers.

"Every time the president did something exceptionally stupid -- which was often enough -- we'd get a spike in sales," Red Corn says. "That really catapulted my business." 

Mocking U.S. presidents and other elected leaders is as old as the nation itself, of course. But Bush's approval rating, which has hovered around 30 percent for more than a year, makes him the least popular president since Richard Nixon at the height of Watergate -- statistically speaking, at least. That has created a booming market for merchandise poking fun at the 43rd president.

Aided by the Internet, fledgling entrepreneurs like Red Corn have seized on the president's unpopularity, offering everything from faux campaign buttons to Bush-shaped dog treats. Many of these businesses started out as political pranks geared more toward venting opposition to the president's domestic and foreign policies than turning a profit. Yet, buoyed by strong demand, more than a few have since become successful, full-time ventures.  

"It went very quickly from my own frustrations into a very real business," says Elliott Nachwalter, a Manchester, Vt.-based pipe maker who has sold more than $1 million in buttons, bumper stickers, golf balls, and other merchandise emblazoned with "1.20.09" -- Bush's final day in office. In addition to his own website,, Nachwalter has landed more than 600 retail accounts in the last three years. "Clearly, it was a frustration that a lot of people shared," he says. 

There is one big problem, however -- the party is almost over. With Bush's time in office coming to an end and media attention focused squarely on the election to succeed him, these successful retailers are being forced to seek new directions in order to keep their businesses going.

"It's winding down," says John Wooden, the founder of, a Brooklyn, N.Y.-based Bush parody site that features an "officious" gift shop offering anti-Bush thongs, boxers, Christmas ornaments, and other products. Wooden, a veteran Web publisher who started rolling out anti-Bush buttons and T-shirts in 2002, says demand peaked about a year ago. "We've seen a precipitous decline in recent months," he says.

Richard Parr, the owner of, says he isn't sure what he'll do with his site after the November election. He currently has more than 300 different stickers in stock.

"Sales have already been pretty slow, since Bush is pretty much over," says Parr, a Santa Monica, Calif.-based auto parts manufacturer. "He's been such an easy target. It's going to be hard for some businesses to adjust."     

Perhaps no one feels that pressure more than Nachwalter. Like the president himself, his novelty countdown products come with a built-in expiration date. In the short term, Nachwalter is hoping a flurry of last-minute legacy building, farewell junkets, and end-of-an-era media stories will spark a final run on sales. He's also working on re-jigging the countdown -- for which he holds a trademark -- from signaling Bush's last day in office to a celebration of what he hopes will be Barack Obama's first day on the job.

Yet beyond that, Nachwalter plans to leverage the experience he's gained with manufacturers, trade shows, and retailers to pursue a less political business idea, one he's keeping under wraps. "That's been an important learning curve with all of this," he says.

So will any of Bush's potential replacements provide a similar windfall? According to CafePress, a San Mateo, Calif.-based e-commerce marketplace for independent retailers, sales of political merchandise -- both pro and con -- rise and fall along with public sentiment. "Merchandise sales are in many ways the best poll," says CafePress CEO Fred Durham. Earlier this year, sales of Obama products outpaced those of Hillary Clinton on the site, corresponding with wins in the Democrat primary cycle.

By the same token, retailers are quick to adapt to shifting political grounds. Within days of John McCain's Republican primary victory in New Hampshire, merchants on CafePress were selling "The Mac is Back" T-shirts and hats. After Clinton cried during an interview on the campaign trail, "Cry Baby for President" stickers went on sale.

Having spent eight years in the White House already, during which she became a favorite target of the right, Clinton seems most likely to generate her own cottage industry. Online retailers are already getting a boost from the primaries with everything from "Even Bill Doesn't Want Her" coffee mugs to donkey-shaped bubblehead dolls.

For his part, Red Corn is looking beyond 1600 Pennsylvania Avenue -- bringing in extra money from his printing press, along with other graphic design work, when his own T-shirt sales are down. He's also expanded his own designs to cover a wider range of issues, clearing up to $6,000 in sales on an average month.

"I made a conscious effort to shift the material away from politics to environmental and anti-petroleum messages," he says. Today, only three of Red Corn's 40 designs take a direct swipe at the president.

"Right now," he says, "all the Bush stuff is on clearance."