After centuries of writing with quills dipped in ink, people in the 1800s began embracing fountain pens with internal ink reservoirs that were filled with eyedroppers. Almost until the end of the century, fountain pens were notoriously fickle devices. They routinely leaked and the flow of ink onto the writing surface was uneven.

An insurance salesman named Lewis Waterman solved the problem of leaks and poor ink distribution in 1884 when he patented a nib (the pen’s metal tip) with hair-thin grooves that allowed air to circulate to the ink reservoir, thus ensuring a smooth and steady flow.

By 1888, Waterman was selling 5,000 pens a year—sales would climb to 1,000 pens a day the year he died in 1901. In 1905, the company became the first pen manufacturer to rivet a clip onto its pen caps so that it could be easily carried right side up in a pocket. Two years later, Waterman introduced a "safety" fountain pen that could be carried in any position, even upside down, without spilling any of its ink. Advertisements from the period show pens loose in a coat pocket, lest consumers miss the point...

Conklin Pen Company made one of the first self-filling fountain pens of the early 1900s. Its Crescent Filler was endorsed by none other than Samuel Clemens, but that was not enough to slow down the public’s acceptance of Sheaffer’s lever fill pen and Parker’s button filler—Conklin would abandon the Crescent in the 1920s and switch to a lever device for filling its pens with ink.

Conklin’s Durograph pens were only made for about a year in 1923, in both Crescent and lever models, making them very collectible. These fat pens had flat tops, with bodies of hard black or red rubber. In 1924, Durographs were redesigned and rebranded as Enduras. A bit smaller than the Durographs, the Enduras came in ebony black, mottled blue, and leaf green, as well as black-and-pearl and black-and-gold. Just in time for the Great Depression, the company introduced its Nozac pen, which featured a "word gauge" to give writers a sense of how much ink was left in a pen.

Other fountain-pen manufacturers from this era include Mabie, Todd & Company, whose top model was the Swan, and Moore Pen Company, whose Maniflex pens had gorgeous tiger-eye bodies. Aiken Lambert made pens with engraved, gold-filled or silver bodies; Gold Bond and John Holland made pens with equally beautiful plastic bodies; and Wahl pens ranged from metal to hard rubber, both of which featured Greek key patterns on their seductive surfaces—its Doric pens from the 1930s are considered some of the loveliest ever made.

One of the biggest pen companies of the first half of the 20th century was Parker. Founded in 1889, a few years after Waterman, Parker first made a name for itself in 1905 with its "Lucky Curve" pens. The Jack Knife Safety pen arrived in 1911. Its cap could be screwed down to the pen’s body, making it ink-tight. One especially prized model had a transparent, amber, Bakelite body. The Jack Knife would evolve into the "Big Red" Duofold in 1921, which was advertised to "rival the beauty of the scarlet tanager."

As already mentioned, Sheaffer was another major player in the 1920s. Sheaffer pens were roughly three times as expensive as most pens of the 1920s, but they had gold nibs that were guaranteed for life and its jade green pen (made of a plastic it called "Radite") was highly desired by businessmen looking for a superior writing instrument that was also a status symbol. In 1924, the famous Sheaffer white dot began to appear on the caps of its pens, and by the following year, the company owned 25 percent of the fountain-pen market.

Conklin did not survive to do business in the post-war era, but Parker did. The company’s biggest hit was one of the most collectible pens known, the Parker 51. Its Lucite body was sleek, while its cap resembled the nosecone of a fighter plane (not coincidentally—Lucite had been used for the canopies of fighter planes). No surprise, then, that the Parker 51 was used to sign the peace treaty between the U.S. and Japan at the end of World War II.

Sheaffer also made it into the 1940s and 1950s. Its Crest Triumph appeared in 1942, and its Snorkel a decade later allowed users to fill their pens through a retractable tube behind the pen’s tip. The PFM (Pen For Men) was released in the late 1950s, and although collectors love it today, it was not very successful at the time.

As for Wahl, it became Eversharp. Its Streamline Moderne-style Skyline was made in large numbers, except for those in 14-karat gold, which are prized by collectors. As for Waterman, the company that had begun the fountain-pen revolution, it had entered the war years with its expensive One Hundred Year pen. In the 1950s, it introduced the C/F, the first modern cartridge fountain pen. Once again, Waterman had a technological edge over its competitors (in this case, the Sheaffer Snorkel and Parker 51), but it could never quite compete in the court of public opinion.

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