Beebe was born in Wakefield, Massachusetts, to a prominent Boston family. Beebe attended both Harvard University and Yale University. During his tenure at boarding school and university, Beebe was known for his numerous pranks. One of his more outrageous stunts included an attempt at festooning J. P. Morgan's yacht Corsair with toilet paper from a chartered airplane. His pranks were not without consequence and he proudly noted that he had the sole distinction of having been expelled from both Harvard and Yale, at the insistence, respectively, of the president and dean of each. Beebe earned his undergraduate degree from Harvard in 1926, only to be expelled during graduate school.

During and immediately after obtaining his degree from Harvard, Beebe published several books of poetry, but eventually found his true calling in journalism. He worked as a journalist for the New York Herald Tribune, the San Francisco Examiner, the Boston Telegram, and the Boston Evening Transcript and was a contributing writer to many magazines such as Gourmet, The New Yorker, Town and Country, Holiday, American Heritage, and Playboy. Beebe re-launched Nevada's first newspaper, the Territorial Enterprise, in 1952.

Beebe wrote a syndicated column for the New York Herald Tribune from the 1930s through 1944 called This New York. The column chronicled the doings of fashionable society at such storied restaurants and nightclubs as El Morocco, the 21 Club, the Stork Club, and the Colony. Mr. Beebe is credited with popularizing the term "cafe society" which was used to describe the people mentioned in his column.

In 1950, Beebe and his long-time friend and partner, photographer Charles Clegg, moved to Virginia City, Nevada, where they purchased and restored the Piper family home and later purchased the dormant Territorial Enterprise newspaper. The newspaper was relaunched in 1952 and by 1954 had achieved the highest circulation in the West for a weekly newspaper. He and Clegg co-wrote the "That Was the West" series of historical essays for the newspaper.

In 1960 Beebe began work with the San Francisco Chronicle where he wrote a syndicated column, This Wild West. During the six years that he wrote the column, Beebe covered such topics as economics, politics, journalism, religion, history, morals, justice, finance, and travel.

Beebe was a noted gourmand. He had his own column "Along the Boulevard," in Gourmet, and wrote extensively for Holiday, and Playboy about restaurants and dining experiences around the world. Some of the restaurants he covered include The Colony, The Stork Club, The Pump Room, the 21 Club, Simpson's-in-the-Strand, and Chasen's. A noted wine aficinado, he was a member of the Confrérie des Chevaliers du Tastevin.

In addition to his work as a journalist, Beebe wrote over 30 books. His books dealt primarily with railroading and café society. Many of his railroad books were written with his longtime companion Charles Clegg.

Beebe was inducted into the Nevada Writers Hall of Fame in 1992.

Along with Clegg, Beebe owned two private railcars, the Gold Coast and The Virginia City. The Gold Coast, Georgia Northern / Central of Georgia No. 100, was built in 1905 and is now at the California State Railroad Museum. After Beebe and Clegg purchased The Virginia City they had it refurbished and redecorated by famed Hollywood set designer Robert T. Hanley in a style known as Venetian Renaissance Baroque. Beebe in the Virginia City The Virginia City has been restored and currently operates as an excursion carriage.

Beebe was also a noted partisan of the Cunard Line and passenger liner travel in general. He wrote several articles about trans-Atlantic passage on Cunard ships during the "Golden Era" of the 20's, 30's and 40's.