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10 of the Most Famous U.S. Postage Stamps in History

Once upon a time, to mail a letter, the sender would have to go to a post office and the postmaster would mark the postage in the top right corner of the envelope based on how many pieces of paper were inside and the distance it would have to travel. The cost could be paid by the sender, receiver, or split between the two.

The idea of a prepaid uniform rate first appeared in the U.K. in 1840, and by 1842, a private U.S. mail carrier, operated by Alexander M. Greig, released the nation’s first adhesive stamp. The United States Postal Service (USPS) soon bought the business from Greig, and by 1847, Congress authorized the use of stamps, with the first ones going on sale that summer: a 5-cent stamp with Benjamin Franklin and a 10-cent stamp with George Washington.

For the first few years of the program, Franklin  — who established the USPS and became its first postmaster general — and Washington were the only people featured on stamps. In 1856, however, the USPS switched things up and introduced a stamp that featured Thomas Jefferson.

Nowadays, stamps can depict everything from notable people and iconic landmarks to art and pop culture characters. Here, we look at some of the most notable American stamps throughout history.

Inverted Jenny 24-Cent Stamp

Closeup still life of the first U.S. air mail stamp, featuring a biplane flying upside down.
Credit: Blank Archives via Getty Images

The 1918 stamp with a red frame and blue plane on it was never meant to take flight the way it did. But as soon as William T. Robey, a 29-year-old stockbroker’s clerk, got his hands on a sheet of a hundred of the 24-cent stamps during his lunch break, he knew that he had hit the jackpot.

In a rare printing mistake, the frame and type were all right side up, but the plate with the image of the Curtiss plane was upside down. It was such a huge deal that federal agents went on the hunt for them. The Bureau of Printing and Engraving had caught the mistake and destroyed all but one sheet that slipped by the inspection team and into Robey’s hands.

Though he paid the face value of $24 for the sheet, he sold it for $15,000 to a dealer who then sold it for $20,000 to Colonel Edward H.R. Green. Green then sold 96 of the stamps one-by-one and kept a quartet with the plate number — called a plate block — intact, and it eventually was acquired by fashion designer Stuart Weitzman, until he auctioned it off at Sotheby’s in June 2021 for $4.9 million.

Hawaiian Postage 2-Cent Stamp

Called the “costliest publicly sold single stamp in history” by Life magazine in 1963, only 15 copies of this rare stamp — used by Christian missionaries writing home from the Hawaiian islands — exist.

Issued by the kingdom of Hawaii in 1851 before it became the 50th state in 1959, the stamp itself is fairly plain, with a single basic green ink shade. All it says are the words “Hawaiian Postage” on the top and “Two cents” at the bottom with a numerical two in a lattice frame — yet its true worth was in the details. Life went on to say that “this, pound for pound, is the most valuable substance on earth.”

Young Elvis Presley 29-Cent Stamp

Commemorative stamp bearing the likeness of a youthful Elvis Presley
Credit: AFP via Getty Images

The “most popular U.S. commemorative stamp of all time” was a matter of public opinion. The year before this 1993 stamp was released, the USPS put out a poll, asking the public to vote on either a young Elvis Presley, with slicked-back hair and a knowing smirk, or an older version of the King, with his trademark white collar popped.

More than three-quarters of the voters preferred the more youthful look, and the stamp was dedicated at Graceland on what would have been Elvis’ 58th birthday. The winning design was chosen from 60 designs submitted by eight artists.

The Wrong Bill Pickett 29-Cent Stamp

The Legends of the West stamps that were revealed in 1993 promised to be so popular that five million panes (the sheets that stamps are issued in) were printed and sent out to post offices across the country. One of the stamps featured Black American cowboy Bill Pickett — who invented bulldogging, or the rodeo event of steer wrestling — depicted as a portrait by artist Mark Hess. Hess created the portrait based on a photo of Pickett..

The problem? That original photo wasn’t of Bill — it was actually his brother, Ben. The Pickett family notified postal authorities the following month. But 183 of the sheets had already been sold. So the USPS embraced its mistake in a profitable way — it sold 150,000 of the incorrect panes through a lottery system to help offset the reprinting costs for the corrected Pickett stamp.

Breast Cancer Research 40-Cent Stamp

Postage Stamp with an illustration for Breast Cancer Research with the phrase "fund the fight, find a cure".
Credit: Mirt Alexander/ Shutterstock

In 1997, a law was passed requiring the USPS to sell stamps with a surcharge  — called semipostal stamps — to raise money for worthy causes. The first one was for breast cancer research, but hitting the right vibe proved to be a challenge. Ethel Kessler, the postal service’s art director who happened to be a survivor, reached out to Baltimore illustrator Whitney Sherman, who tried sketches of women in different poses. They chose one appearing to conduct a self-exam, cast upon watercolor-like shades with the words “Fund the fight. Find a cure,” in a circular shape where the breast would be.

Though regular first-class stamps were 32 cents in 1998, these sold for 40 cents each. The stamp was reissued in 2014 for 60 cents each.

To date, the USPS says $92.9 million in revenue has been raised from the sale of 1.08 billion breast cancer stamps, with 70% of the net going to National Institutes of Health and 30% to Research Program at the Department of Defense. Other semipostal stamps have supported vanishing species, Alzheimer’s, and healing PTSD.

Love 8-Cent Stamp

Love and stamps have long been a perfect match — and the first among them is still arguably the most iconic. Artist Robert Indiana had painted the word “Love” for the Museum of Modern Art’s holiday card in 1965 and the USPS asked him to adapt it for a stamp, which was unveiled in the City of Brotherly Love, Philadelphia, Pennsylvania, ahead of Valentine’s Day in 1973. While some thought of the design as too “hippie,” its continued influence is seen in the “love” sculptures of his design all over the world.

It took another nine years for a second “love” stamp to come out, but now they are a regular part of the annual stamp issues, often appearing in multiple designs a year.

Martha Washington 8-Cent Stamp

Stamp depicting a portrait of Presidential First Lady Martha Washington.
Credit: Steve Mann/ Shutterstock

The first First Lady was also the first American woman to be honored with a postage stamp in 1902. Queen Isabella of Spain was the first woman to appear on a stamp — seven stamps, in fact — as part of a series on the Columbia Expedition in January 1893. The third woman honored on a U.S. stamp was Pocahontas, who appeared on a 1907 stamp worth 5 cents, but the fourth woman was again Washington, on a 4-cent stamp in 1923.

National Parks Centennial Stamps

A stamp printed in USA showing Mount McKinley, National Parks Centennial Series, circa 1972.
Credit: Roberto Lusso/ Shutterstock

To honor the National Park Service’s 100th anniversary in 1972, the postal service pulled off a grand commemoration, with four sets of stamps in different denominations.

The series included sets of 2-cent stamps of Cape Hatteras National Seashore, 6-cent stamps of Wolf Trap National Park for the Performing Arts, 8-cent stamps of Yellowstone’s Old Faithful, and 15-cent stamps from Mount McKinley (today, Denali).

Holiday 4-Cent Stamp

Stamp showing an illustration of candles and Christmas wreath, circa 1962.
Credit: Mirt Alexander/ Shutterstock

For years, customers had requested a stamp that depicted the spirit of the holiday card-sending season, and in 1962, the USPS delivered.

First issued in Pittsburgh, Pennsylvania, expectations were so grand that 350 million of these stamps illustrated with a Christmas wreath and candles were printed, which was the largest number of special stamps ever made at the time; those all sold out and by the end of the year, a billion had been printed.

Booker T. Washington 10-Cent Stamp

As part of the famous Americans series, Booker T. Washington — who was born enslaved and became the founder of the Tuskegee Institute — became the first Black American to appear on a postage stamp in 1940.

However, it wasn’t exactly a celebrated moment. “At the time, there was not a lot of need for a 10-cent stamp,” the National Postal Museum’s Daniel Piazza told Smithsonian Magazine, adding that some thought the chosen denomination might be racist. “A 3-cent stamp would have gotten heavy usage, but a 10-cent stamp would not,” he continued. “Supporters of the stamp alleged that he had been put on the stamp to minimize the extent to which the stamp would be purchased or used.”

Featured Image credit: dp3010/ iStock

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