Originally, Captain Easy was a supporting character in the series Wash Tubbs, which focused on the adventures of the zany Washington Tubbs II. On February 26, 1929, Crane introduced the taciturn toughguy Captain Easy, who soon took over the strip. On July 30, 1933, Crane launched Captain Easy, Soldier of Fortune as a Sunday page starring Easy.
Captain Easy was a chivalrous Southern adventurer in the classic adventure-hero mold. After a series of globe-trotting adventures, Easy enlisted in the U.S. Army during World War II, afterwards becoming a private detective.
The Sunday adventures were initially unconnected to those of the Wash Tubbs strip and dealt with Easy's adventures prior to meeting Tubbs. They are considered a tour-de-force by Crane, who crafted layouts intended to be seen as a coherent whole rather than a disparate collection of panels. Comics historian R. C. Harvey described Crane's Sunday page innovation:
'On Sundays, Crane concentrated on Easy, and these pages soon absorbed him. The art chores on the dailies were assigned to others in the NEA bullpen so that Crane could pour his imagination into the weekly installments of Easy's adventures. Crane loved the spacious potential of the Sunday page—as would any graphic artist; and he spent most of his energy here rather than on the less visually challenging dailies. And on the Sunday pages, Crane did some of his finest work. Since he was drawing for the addition of color, Crane shaded these pages very little, so his artwork here is refined to its unembellished essence. And in its essence, Crane's work demonstrates the marvelous precision and telling efficacy of a line so simple it seems naive. But appearances in art are as often deceiving as they are in life. The simplicity of Crane's linework is the ultimate sophistication of irreducible economy, the absolute in purity of graphic expression'.
Crane's Sunday pictures are carefully, lovingly, drawn, every panel composed to tell the story while sustaining the illusion of time and place. And the pages themselves are artful designs, irregular albeit nonetheless pleasing patterns of panels rather than uniform grids. But these layouts are not simply designs: they were devised to give visual impact to the story. When Crane drew Easy at the brink of a cliff, he gave depth to the scene by depicting it in a vertical panel that is two- or three-tiers tall. When Easy leads a cavalry charge or paddles a canoe down a lazy river, the panel is as wide as the page, giving panoramic sweep to the scene depicted.
Unfortunately, in 1937, the Newspaper Enterprise Association syndicate, which employed Crane and owned the strip, introduced a new policy requiring Sunday pages designed so the panels could be rearranged into different formats. Crane then turned the Sunday pages over to his assistant Leslie Turner, so he could concentrate on the daily strip. The Tubbs and Easy characters were owned by NEA, and in 1943, Crane abandoned his strips and exited NEA to begin Buz Sawyer, a strip he would own outright.
After Crane's departure, Turner took control of the strips, with his assistant Walt Scott drawing the Sunday page. Easy was in the Army by that time, and Tubbs had an increasingly unimportant role, so both daily and Sunday strips displayed the name Captain Easy in 1949.
Scott drew Captain Easy through the 1940s and 1950s. Mel Graff began ghosting it in 1960. When Turner retired in 1969, the strips passed to his assistants, Bill Crooks and Jim Lawrence. Mick Casale came aboard in 1982 and lasted until the series was discontinued in 1988.
Before the Sunday Captain Easy, there was a short-lived Wash Tubbs Sunday third, which began with gags featuring Tubbs and later puzzles for children. It ran from 10 May 1931 to 9 July 1933. Captain Easy appeared in one strip.