His contemporaries—Ernest Hemingway, Virginia Woolf, and F. Scott Fitzgerald—all professed strong admiration for his writing, and author John O'Hara directly attributed his understanding of dialogue to him.

[3] Two years later, Lardner was in St. Louis, writing the humorous baseball column Pullman Pastimes for Taylor Spink and the Sporting News.

In 1913, Lardner returned to the Chicago Tribune, which became the home newspaper for his syndicated column In the Wake of the News (started by Hugh Keough, who had died in 1912).

In 1916, Lardner published his first successful book, You Know Me Al, an epistolary novel written in the form of letters by "Jack Keefe", a bush-league baseball player, to a friend back home.

Journalist Andrew Ferguson wrote that "Ring Lardner thought of himself as primarily a sports columnist whose stuff wasn't destined to last, and he held to that absurd belief even after his first masterpiece, You Know Me Al, was published in 1916 and earned the awed appreciation of Virginia Woolf, among other very serious, unfunny people."

He also continued to write follow-up stories to You Know Me Al, with the protagonist of that book, the headstrong, egotistical but gullible Jack Keefe, experiencing various ups and downs in his major league career and in his personal life.

Lardner also wrote skits for the Ziegfeld Follies and a series of brief nonsense plays that ridiculed the conventions of the theatre, using zany humor and outrageous, impossible stage directions, such as "The curtain is lowered for seven days to denote the lapse of a week.

Other collaborators of note included Aubrey Stauffer, Jerome Kern on Very Good Eddie (1915), and Vincent Youmans—with whom he toiled on the Ziegfeld–Marilyn Miller–Asstores musical Smiles (1930).

Ring's second born, James Lardner, worked as a newspaperman before he was killed in the Spanish Civil War fighting with the International Brigades.

The youngest, David Lardner, worked for The New Yorker as a general reporter and war correspondent before he was killed by a landmine near Aachen, Germany on October 19, 1944, less than one month after his arrival in Europe.

Lardner died on September 25, 1933, at the age of 48 in East Hampton, New York, of a heart attack due to complications from tuberculosis.