My introduction to Loujon Press occurred during a routine pull for a patron. Kneeling to check a call number, I noticed another book peeking out from behind a few Hollinger boxes. There among the uniformity of the items arranged on the shelf sat a book donning a paper dust jacket in a distinct shade of goldenrod yellow; after just one look, I knew that I had stumbled upon something special.
Diving into the history of Loujon Press and The Outsider reveals the story of a wildly creative couple who were as dedicated to their art as they were to each other. Jon Edgar Webb was born on February 1st, 1905, in Cleveland, Ohio. He began his writing career as a reporter for the Cleveland News and the Toronto Star. Louise Dorothy Madaio was born in Cleveland, Ohio on April 29th, 1916. Fashionably eccentric, Gypsy Lou was a lifelong creative who was well-known for her art, particularly her paintings.
Gypsy Lou and Jon Webb met in the mid-1930s; at the time he was writing a novel, and she was an emerging songwriter. They instantly identified the other as a kindred spirit and their relationship developed rapidly. Jon and Gypsy Lou married in 1939. In 1940, after a brief stint in St. Louis, the couple made their way to New Orleans.
By the early 1950s, the couple had achieved their dream – they were working artists earning a (modest) living from Jon’s writing and Gypsy Lou’s paintings, which she sold from a stand in the French Quarter. The Webbs spent nearly a decade connecting with members of the vibrant underground writing scene and befriended several purveyors of little magazines, including the editors of New Orleans Poetry Review. Driven by their personal passions for the creative arts and the future of American literature, the Webbs embarked on a journey to produce their own little magazine dubbed The Outsider.
Loujon Press published the inaugural issue of The Outsider in 1961. Its cover features a tightly cropped portrait of Gypsy Lou staring directly into the camera lens with her chin resting on her closed fist. Bold, blocky, cut-and-paste letters spelling out “The Outsider” follow the arch of her left eyebrow then swoop down to obscure her right eye. Even with just one eye visible, Gyspy Lou’s piercing gaze draws you in. For their local audience in New Orleans, using Gypsy Lou’s face on the cover was a strategic selling point that was sure to grab the attention of readers who were familiar with Gypsy Lou as a mainstay of the French Quarter art scene.
Jon once stated that Gypsy Lou would be on every cover of The Outsider – indeed she did grace the cover of issue two and even makes a sneaky appearance on the cover of issue three where she is featured in a framed, painted portrait which hangs just above Charles Bukowski’s head.
In addition to serving as Editor and Associate Editor, Jon and Gypsy Lou hand-printed, collated, hand-bound, and self-distributed every single publication themselves from their apartment-studio. Carefully considering all aspects of each publication including layout, design, and unique finishings, production was physically demanding and time consuming. However, such attention to detail ensured that each publication was imbued with distinct handcrafted qualities that were paramount to their publishing ethos.
All 3,100 copies of issue one of The Outsider were printed by Gypsy Lou and Jon on an old Chandler and Price printing press acquired from Tulane University. On the back inside cover they provided detailed statistics on the labor and production process noting that at a rate of roughly one page per day it took them “about 4,500 hours to get the job done…” These statistics were coupled with a plea for support as they worked to earn enough money to replace their C & P press with a motorized press. They made a limited-time offer of 100 life-time subscriptions to the magazine to offset the cost, and it worked.
Little magazines of the mid-20th century are largely defined by their use of low-cost spirit duplicators such as the ditto machine or stencil duplicators like the mimeograph machine. These machines are intrinsically linked to a flurry of inexpensive publications produced throughout the 1960s, an era known as the Mimeograph Revolution. As such, the handset, hand printed, and handbound nature of each issue of The Outsider likely caught the eye of more than a few readers. Just to be certain, the Webbs highlighted their labor and overall workmanship through the inclusion of a message proclaiming this very fact with “PRINTED BY HAND In New Orleans USA” usually found stamped in red ink on the front flyleaf of each issue of The Outsider, as shown in the images below.
Their production process was grueling and expensive, contributing greatly to the couple’s ever-looming financial struggles. To remedy this, Gypsy Lou took over typesetting for The Outsider – a skill that saved them about $2.00 per page. This was a significant amount as it is estimated that each issue of The Outsider cost roughly $7.00 to produce, a price equivalent to about $75.00 in 2025. Yet they sold it for $1.45 per copy – operating at a significant deficit!
In addition to platforming up-and-coming writers, issue #1 features an impressive list of established talent, uniting poets and writers from several literary scenes — from the San Francisco Beats to the Black Mountain Poets. The starting roster includes Charles Bukowski, William S. Burroughs, Robert Creeley, Lawrence Ferlinghetti, Langston Hughes, Charles Olson, Diane Di Prima, and many more.
The Webbs took great pride in the writers they assembled for their very first issue. Alongside a comprehensive “Contributors” section, they created two collages featuring the name and portrait of nearly every one of them. A third collage, pictured above, is featured on the issue’s back cover; each image is cut out and overlaid on top of the cover image of Gypsy Lou with “The Editor,” Jon, proudly watching over from the upper right corner. The crafty quality of these collages further showcases the handmade nature of the magazine. Along with the inclusion of their own photos, artwork, and writing, the Webbs’ presence is quite literally embedded throughout the magazine, from cover to cover.
Building on their support for artists and creatives issue two, issue three, and double-issue four/five of The Outsider feature visual art from the likes of Ray Johnson and Kenneth Patchen – artists whose work skirts definition, blurring the line between writer and artist. Later issues also continue to feature drawings and writings from both Jon and Gypsy Lou.
After acquiring a motorized press, the Webbs were well equipped to tackle future issues of The Outsider, alongside even more ambitious projects, and expanded their focus to include elevated, fine press books. Having published his writing in every issue of The Outsider, Charles Bukowski had established a relationship with Jon and Gypsy Lou. Given the Webbs’ fervent support of Bukowski’s work, it was a natural step for Loujon Press to publish two of his earliest works: It Catches My Heart in Its Hands (1963) and Crucifix in a Deathhand (1965). Loujon Press also published two books by Henry Miller: Order and chaos chez Hans Reichel (1966) and Insomnia: or, The devil at large: a first edition book & portfolio (1971). Each of these elevated editions were made with a variety of handmade paper imported from Italy and Japan. The Webbs also incorporated more experimental material such as the thin pieces of smooth cork featured in the “Cork Edition” of Order and chaos chez Hans Reichel, shown below.
While Gypsy Lou had hoped to keep it going, Loujon Press all but ceased operation with Jon’s passing in 1971. Having received renewed interest and dedicated scholarship in recent years, Jon and Gypsy Lou Webb have been rightfully established as important figures of the 1960s American literary tradition.
The Rare Book and Special Collections Division’s issues of The Outsider were originally cataloged as American Literature. However, after spending more time with the magazines, and other Loujon Press titles, it became clear that Loujon Press should be moved into the division’s Press Collection, which has a focused interest on the unique quality of craftsmanship inherent to typography and letterpress printing.
The division holds a complete run of all titles published by Loujon Press. These materials are available for research in the Rare Book Reading Room. For more information, or to schedule a visit, please send a query to the reference staff via Ask-A-Librarian.
Sources and Further Reading
Bukowski, Charles. (1963). It catches my heart in its hands : new and selected poems 1955-1963. Loujon Press.
Bukowski, Charles. (1965). Crucifix in a deathhand: new poems 1963-65. Loujon Press.
Miller, Henry. (1966). Order and chaos chez Hans Reichel. Loujon Press.
Miller, Henry. (1971). Insomnia: or, The devil at large : a first edition book & portfolio. Loujon Press.
Webb, Gypsy Lou. Webb, J. The Outsider. (1961 – 1969). Loujon Press.
Weddle, Jeff. Bohemian New Orleans: The Story of the Outsider and Loujon Press. University Press of Mississippi.
A special thank you to the Historic New Orleans Collection for allowing a few of their Loujon Press images to be used in this blog post.