Benchley was later known for writing elaborately fanciful autobiographical statements about himself (at one time asserting that he wrote A Tale of Two Cities before being buried at Westminster Abbey).

[4] His father served with the Union army for two years during the Civil War and had a four-year hitch in the Navy before settling again in Worcester, marrying and working as a town clerk.

[5][3] Robert's older brother Edmund (born March 3, 1876)[6] was a 4th year cadet at West Point in 1898 when his class was graduated early to support preparations for the Spanish–American War; he was killed July 1 at the Battle of San Juan Hill.

His humor and style began to reveal themselves during this time: Benchley was often called upon to entertain his fraternity brothers, and his impressions of classmates and professors became very popular.

Owing to an academic failure during his senior year due to an illness,[18] Benchley would not receive his Bachelor of Arts from Harvard until the completion of his credits in 1913.

His shortcoming was the submission of a "scholarly paper" – which Benchley eventually rectified by a treatise on the U.S. – Canadian Fisheries Dispute, written from the point of view of a cod.

[17] Benchley did copy work for the Curtis Company during the summer following graduation, while doing other odd service jobs, such as translating French catalogs for the Boston Museum of Fine Arts.

The liberty gave his work new life, and the success of his pieces in the magazine convinced his editors to give him a signed byline column in the Tribune proper.

When a rumored vacancy for an editorial job at Vanity Fair failed to happen, Benchley decided he would continue freelancing, having made a name for himself at the magazine.

The two were given a good deal of freedom, but Benchley's coverage of the war and emphasis on African-American regiments as well as provocative pictorials about lynching in the southern United States earned him and Gruening scrutiny from management.

Eventually, he began lobbying gently for Benchley to compile his columns into book form, and, in 1921, was delighted when the result of his nagging - Of All Things - was published.

[citation needed] Benchley began at Vanity Fair with fellow Harvard Lampoon and Hasty Pudding Theatricals alumnus Robert Emmet Sherwood and future friend and collaborator Dorothy Parker, who had taken over theatre criticism from P. G. Wodehouse years earlier.

When the editorial managers went on a European journey, the three took advantage of the situation, writing articles mocking the local theatre establishment and offering parodic commentary on a variety of topics, such as the effect of Canadian ice hockey on United States fashion.

These issues contributed to a general deterioration of morale in the offices, culminating in Parker's termination, allegedly due to complaints by the producers of the plays she criticised in her theatrical reviews.

[44] In April 1920, Benchley obtained a job with Life writing theatre reviews, which he would continue doing regularly through 1929, eventually taking complete control of the drama section.

[46] Benchley had continued to receive positive responses from his performing, and in 1925 he accepted a standing invitation from movie producer Jesse L. Lasky for a six-week term writing screenplays at $500.

Worn down, Benchley began his next commitment, motion-picture versions of his pieces The Treasurer's Report and The Sex Life of the Polyp, filmed in 1928 by Fox with its new Movietone sound system.

While Benchley, along with many of his Algonquin acquaintances, was wary of getting involved with another publication for various reasons, he completed some freelance work for The New Yorker during the first few years, and was later invited to be newspaper critic.

He continued to work in Hollywood a writer and performer, contributing dialogue for the Stuart Palmer mystery Murder on a Honeymoon (1935) and appearing in the lavish feature-length production China Seas for Metro-Goldwyn-Mayer, featuring Clark Gable, Jean Harlow, Wallace Beery, and Rosalind Russell; Benchley's character was a slurring drunk throughout the movie.

Upon its completion, MGM invited Benchley to write and perform in a short production inspired by a Mellon Institute study on sleep commissioned by the Simmons Mattress Company.

[55] How to Sleep was named Best Short Subject at the 1935 Academy Awards, and MGM kicked off an entire series of situation-comedy reels, each 10 minutes in length, showing Benchley giving mock-instructional lectures (How to Be a Detective, How to Rest, etc.)

While starring in his short subjects Benchley returned to feature films, cast in the revue Broadway Melody of 1938 and in his largest role to that point, the lightweight comedy Live, Love and Learn.

Following the printing of two books of his old New Yorker columns, Benchley gave up writing for good in 1943, signing one more contract with Paramount for feature films in December of that year.

In this capacity Paramount cast him in the 1945 Bob Hope-Bing Crosby comedy Road to Utopia; Benchley interrupts the action periodically to "explain" the nonsensical storyline.

On April 22, 1945, he guest starred on the Blue Network's (soon to be ABC) top-rated radio series The Andrews Sisters Show, sponsored by Nash motor cars & Kelvinator home appliances.

Initially consisting of Benchley, Dorothy Parker, and Alexander Woollcott during their time at Vanity Fair, the group eventually expanded to over a dozen regular members of the New York media and entertainment, such as playwrights George S. Kaufman and Marc Connelly and journalist/critic Heywood Broun, who gained prominence due to his positions during the Sacco and Vanzetti trial.

While some of his pieces would not have been out of place in a crackerbarrel-style presentation, Benchley's reliance on puns and wordplay resonated more with the literary humorists, as shown by his success with The New Yorker, known for the highbrow tastes of its readers.

This character was apparent in Benchley's Ivy Oration during his Harvard graduation ceremonies,[68] and would appear throughout his career, such as during "The Treasurer's Report" in the 1920s[69] and his work in feature films in the 1930s.

"[71] His lighter fare did not hesitate to touch upon topical issues, drawing analogies between a football game and patriotism, or chewing gum and diplomacy and economic relations with Mexico.

[74] The longer, plot-driven shorts, such as Lesson Number One, Furnace Trouble, and Stewed, Fried and Boiled, likewise show a Benchley character overmatched by seemingly mundane tasks.