Although Benchley was known for misleading and fictional autobiographical statements about himself (at one point asserting that he wrote A Tale of Two Cities before being buried at Westminster Abbey), he actually was the great-grandchild of the founder of Benchley, Texas: Henry Wetherby Benchley who was jailed for his help with the Underground Railroad. Robert Benchley was born on September 15, 1889 in Worcester, Massachusetts, to Charles and Maria Benchley.

's older brother, Edmund, was rushed to the Spanish-American War days after graduation from West Point (1898), and was a casualty almost immediately. The Benchley family was attending a public Fourth of July picnic when a bicycle messenger brought the notification telegram. In unthinking, stunned reaction, Maria ("Jenny") Benchley cried out "Why couldn't it have been Robert?!", then standing by her side at the age of nine. Mrs. Benchley apologized profoundly and tried hard to atone for the remark. Edmund's death had a considerable effect upon Robert's life. Lillian Duryea, the bereaved, wealthy yeast heiress and fiancee of Edmund, undertook the funding of Robert's education; she made him a loan which, after he began to make money, she later called due. (There is no evidence to support speculation that Lillian had an inappropriate relationship with Robert.) One theory holds that Edmund's death in battle seeded pacifist leanings in his writings. The period, however, was full of literary abreaction to the Great War, and Benchley was aware of the published remorse of A.A. Milne.

Robert Benchley married Gertrude Darling; they met while Benchley was in high school in Worcester, engaged during his senior year at Harvard, married in June 1914, and their first child, Nathaniel Benchley was born a year later. A second son, Robert Benchley, Jr., was born in 1919. Nathaniel became a writer himself, and penned a biography of his father in 1955 as well as becoming a well-respected children's book author. Nathaniel had talented sons as well: Peter Benchley was best known for the book Jaws (which inspired the film of the same name), and Nat Benchley wrote and performed in an acclaimed one-man production based on Robert's life.

Education

Robert grew up and attended school in Worcester and was involved in academic and traveling theatrical productions during high school. Thanks to financial aid from his late brother's fiancee, Lillian Duryea, he could attend Phillips Exeter Academy in Exeter, New Hampshire for his final year of high school. Benchley reveled in the atmosphere at the Academy, and he remained active in creative extracurricular activities, thereby damaging his academic credentials toward the end of his term.

Benchley enrolled at Harvard University in 1908, again with Duryea's financial help. He joined the Delta Upsilon fraternity in his freshman year, and continued to partake in the camaraderie that he had enjoyed at Phillips Exeter while still doing well in school. He did especially well in his English and government classes. His humor and style began to reveal itself during this time; Benchley was often called upon to entertain his fraternity brothers, and his impressions of classmates and professors became very popular. His performances gave him some local fame, and most entertainment programs on campus and many off-campus meetings recruited Benchley's talents.

During his first two years at Harvard, Benchley worked with the Harvard Advocate and the Harvard Lampoon. He was elected to the Lampoon's board of directors in his third year. The election of Benchley was unusual, as he was the publication's art editor and the board positions typically fell to the foremost writers on the staff. The Lampoon position opened a number of other doors for Benchley, and he was quickly nominated to the Signet Society meeting club as well as becoming the only undergraduate member of the Boston Papyrus Club at the time.

Along with his duties at the Lampoon, Benchley acted in a number of theatrical productions, including Hasty Pudding productions of The Crystal Gazer and Below Zero. Benchley kept these achievements in mind as he began to contemplate a career for himself after college. Charles Townsend Copeland, an English professor, recommended that Benchley go into writing, and Benchley and future Benchley illustrator Gluyas Williams from the Lampoon considered going into freelance work writing and illustrating theatrical reviews. Another English professor recommended that Benchley speak with the Curtis Publishing Company; but Benchley was initially against the idea, and ultimately took a position at a civil service office in Philadelphia. Owing to an academic failure in his senior year due to an illness, 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. He took a position with Curtis shortly after he received his diploma.

Early Professional Career

Benchley did copy work for the Curtis Publishing Company during the summer following graduation (1913) while doing other odd service jobs, such as translating French catalogs for the Boston Museum of Fine Arts. In September 1913 he was hired by Curtis as a full-time staff member, preparing copy for its new house publication, Obiter Dicta. The first issue was roundly criticized by management, who felt it was "too technical, too scattering, and wholly lacking in punch." Things did not improve for Benchley and Obiter Dicta, and a failed practical joke at a company banquet further strained the relationship between Benchley and his superiors. He continued his attempts to develop his own voice within the publication, but Benchley and Curtis were not a good match and he eventually left, as Curtis was considering eliminating Benchley's role and Benchley was offered a position in Boston with a better salary.

Benchley held a number of similar jobs in following years. His re-entry into public speaking followed the annual Harvard—Yale football game in 1914, where he presented a practical joke involving "Professor Soong" giving a question-and-answer session on football in Chinese. In what the local press dubbed "the Chinese professor caper", Soong was played by a Chinese-American who had lived in the United States for over thirty years, and pretended to answer questions in Chinese while Benchley "translated." While his public profile rose, Benchley continued with freelance work, which included his first paid piece for Vanity Fair in 1914, titled "Hints on Writing a Book," a parody of the non-fiction pieces then popular. While Benchley's pieces were bought by Vanity Fair from time to time, his consistent work dried up, and Benchley took a position with the New York Tribune.

Benchley started at the Tribune as a reporter. He was a very poor one, unable to get statements from people quoted in other papers, and eventually had greater success covering lectures around the city. He was promised a position at the Tribune's Sunday magazine when it launched, and he was moved to the magazine's staff soon after he was hired, eventually becoming chief writer. He wrote two articles a week; the first a review of non-literary books, the other a feature-style article about whatever he wanted. 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.

Benchley filled in for P. G. Wodehouse at Vanity Fair at the beginning of 1916, reviewing theatre in New York. The experience at Vanity Fair inspired Benchley's fellow staff at the Tribune magazine with creative topics for articles (such as arranging for the producers of The Thirteenth Chair to cast Benchley as a corpse), but the situation at the magazine deteriorated as the pacifist Benchley became unhappy with the Tribune's position on World War I, and the Tribune editors were unhappy with the evolving tone and irreverence of the magazine. In 1917, the Tribune shut down the magazine, and Benchley was out of work again. When a rumored opening for an editorial position at Vanity Fair fell through, Benchley decided he would continue freelancing, having made a name for himself at the magazine.

This freelancing attempt did not start out well, with Benchley selling just one piece to Vanity Fair and accumulating countless rejections in two months. When a job as a press agent for Broadway producer William A. Brady was offered, Benchley took the position against the advice of many of his peers. This experience was a poor one, as Brady was extremely difficult to work for, and Benchley resigned to became a publicity director for the federal government's Aircraft Board at the beginning of 1918. His experience there was not much better, and when an opportunity was offered to return to the Tribune under new editorial management, Benchley took it.

At the Tribune, Benchley, along with new editor Ernest Gruening, was in charge of a twelve-page pictorial supplement titled the Tribune Graphic. The two were given a good deal of freedom, but Benchley's coverage of the war and focus on African-American regiments as well as provocative pictorials about lynching in the southern United States earned him and Gruening scrutiny from management. Amid accusations that both were pro-German (the United States was fighting Germany at the time), Benchley tendered his resignation in a terse letter, citing the lack of "rational proof that Dr. Gruening was guilty of...charges made against him..." and management's attempts to "smirch the character and the newspaper career of the first man in three years who has been able to make the Tribune look like a newspaper."

Benchley was forced to take a publicity position with the Liberty Loan program, and he continued to freelance until Collier's contacted him with an associate editor position. Benchley took this offer to Vanity Fair to see if they could match it, as he felt Vanity Fair was the better magazine, and Vanity Fair offered him the position of managing editor. Benchley accepted, and began work there in 1919.

An often overlooked influence upon Benchley's early professional career was the admiration and friendship of the Canadian economist, academic, and humorist Dr. Stephen Leacock. From Toronto Leacock closely followed the increasing body of Benchley's published humor and wit, and opened correspondence between them. Leacock admitted to occasional borrowing of a Benchley topic for his own reflection and writings. Eventually, he began lobbying gently for Robert Benchley to compile his columns into book form, and in 1922 was delighted with the result of his nagging.

Vanity Fair and its aftermath

Benchley began at Vanity Fair with fellow Harvard Lampoon alumnus Robert Emmet Sherwood and future friend and collaborator Dorothy Parker, who had taken over theatre criticism from P. G. Wodehouse years earlier. The format of Vanity Fair fit Benchley's style very well, allowing his columns to have a humorous tone, often as straight parodies. Benchley's work was typically published twice a month. Some of Benchley's columns, featuring a character he created, were attributed to his pseudonym Brighton Perry, but most were attributed to Benchley himself. Sherwood, Parker, and Benchley became close, often having long lunches at the Algonquin Hotel. When the editorial managers went on a European trip, 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 hockey on United States fashion. This worried Sherwood, as he felt it could jeopardize his forthcoming raise.

The situation at Vanity Fair deteriorated on the managerial team's return. The management sent out a memo forbidding the discussion of salaries in an attempt to rein in the staff. Benchley, Parker, and Sherwood responded with a memo of their own, followed by placards around their necks detailing their exact salaries for all to see. Management attempted to issue "tardy slips" for staff who were late; on one of these, Benchley filled out, in very small handwriting, an elaborate excuse involving a herd of elephants on 44th Street. 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 skewered in her theatrical reviews. Upon learning of her termination, Benchley tendered his own resignation. Word of it was published in Time by Alexander Woollcott, who was at a lunch with Benchley, Parker, and others. Given that Benchley had two children at the time of his resignation, Parker referred to it as "the greatest act of friendship I'd ever seen."

Following word of Benchley's resignation, freelance offers began piling up. He worked constantly while claiming he was intensely lazy. (According to legend, he submitted a magazine piece titled “I Like to Loaf” two weeks after deadline. His explanatory note: “I was loafing.”) He was offered $200 per basic subject article for The Home Sector, and a weekly freelance salary from New York World to write a book review column three times per week for the same salary he received at Vanity Fair. The column, titled "Books and Other Things," ran for one year and roved beyond literature to mundane topics such as Bricklaying in Modern Practice. Unfortunately for Benchley, however, his writing a syndicated column for David Lawrence drew the ire of his World bosses, and "Books and Other Things" was dropped.

Benchley continued to freelance, submitting humor columns to a variety of publications, including Life (where fellow humorist James Thurber believed Benchley's columns were the only reason the magazine was read). He continued meeting with his friends at the Algonquin, and the group became popularly known as the Algonquin Round Table. In April 1920, Benchley landed a position with Life writing theatre reviews, which he would continue doing regularly through 1929, eventually taking complete control of the drama section. His reviews were known for their flair, and he often used them as a soapbox for issues of concern to him, whether petty (people who cough during plays) or more important (such as racial intolerance).

Things changed again for Benchley a number of years into the arrangement. A theatrical production by the members of the Round Table was put together in response to a challenge from actor J. M. Kerrigan, who was tired of the Table's complaints about the ongoing theatre season. The result was No Sirree! (the name being a pun of the European revue Le Chauve-Souris), "An Anonymous Entertainment by the Vicious Circle of the Hotel Algonquin." Benchley's contribution to the program, "The Treasurer's Report," featured Benchley as a nervous, disorganized man attempting to summarize an organization's yearly expenses. The revue was applauded by both spectators and fellow actors, with Benchley's performance in particular receiving the biggest laughs. A reprise of "The Treasurer's Report" was often requested for future events, and Irving Berlin hired Benchley for $500 a week to perform it nightly during Berlin's Music Box Revue.

Hollywood and The New Yorker call

Benchley had continued to receive positive responses from his performing, and in 1925 he accepted a standing invitation from film producer Jesse L. Lasky for a six-week term writing screenplays at $500. While the session did not yield significant results, Benchley did get writing credit for producing the title cards on the Raymond Griffith silent film You'd Be Surprised, and was invited to do some titling for two other films.

Benchley was also hired to help with the book for a Broadway musical, Smarty, starring Fred Astaire. This experience was not as positive, and most of Benchley's contributions were excised and the final product, Funny Face, did not have Benchley's name attached. Worn down, Benchley moved to his next commitment, an attempt at a talking film version of "The Treasurer's Report." The filming went by quickly, and though he was convinced he was not good, The Treasurer's Report was a financial and critical success upon its release in 1928. Benchley participated in two more films that year: a second talking film he wrote, The Sex Life of the Polyp, and a third starring but not written by him, The Spellbinder, all made in the Fox Movietone sound-on-film system and released by Fox Films. The films enjoyed similar success and were critically acclaimed, and Benchley was signed to a deal to produce more films before heading back to New York to continue writing. As Life would say following his eventual resignation in 1929, "Mr. Benchley has left Dramatic Criticism for the Talking Movies".

During the time that Benchley was filming various short films, he also began working at The New Yorker, which had started in February 1925 under the control of Benchley's friend Harold Ross. 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 over the first few years, and was later invited to be newspaper critic. Benchley initially wrote the column under the pseudonym Guy Fawkes (the lead conspirator in the English Gunpowder Plot), and the column was very well received. Benchley tackled issues ranging from careless reporting to European fascism, and the publication flourished. Benchley was invited to be theatre critic for The New Yorker in 1929, leaving Life, and contributions from Woollcott and Parker became regular features in the magazine. The New Yorker published an average of forty-eight Benchley columns per year during the early 1930s.

With the emergence of The New Yorker, Benchley was able to stay away from Hollywood work for a number of years. In 1931, he was persuaded to do voice work for RKO Radio Pictures for a film that would eventually be titled Sky Devils, and he acted in his first feature film, The Sport Parade (1932) with Joel McCrea. The work on The Sport Parade caused Benchley to miss the fall theatre openings, which embarrassed him (even if the relative success of The Sport Parade was often credited to Benchley's role), but the lure of filmmaking did not disappear, since RKO offered him a writing and acting contract for the following year for more money than he was making writing for The New Yorker.

Benchley on film and "How to Sleep"

Benchley re-entered Hollywood at the height of the Great Depression and the large-scale introduction of the talkie films he had begun working with years before. His arrival put him on the scene of a number of productions almost instantly. While Benchley was more interested in writing than acting, one of his more important roles as an actor was as a salesman in Rafter Romance, and his work attracted the interest of MGM, who offered Benchley a lot of money to complete a series of short films. Benchley, who had also been offered a syndicated column by Hearst, was able to film the shorts in New York and keep up with his new column. Before heading back to New York, Benchley took a role in the feature film Dancing Lady, which also featured Joan Crawford, Clark Gable, Fred Astaire, Nelson Eddy, and the Three Stooges.

In 1933, Benchley returned to Hollywood, completing the short films Your Technocracy and Mine for Universal Pictures, How to Break 90 at Croquet for RKO, and the lavish feature-length production China Seas for Metro-Goldwyn-Mayer, starring Clark Gable, Jean Harlow, Wallace Beery, and Rosalind Russell; Benchley's character was slurring drunk throughout the movie. Upon 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. The resulting film, How to Sleep, was filmed in two days, and featured Benchley as both the narrator and sleeper, the latter a role Benchley claimed was "not much of a strain, as [he] was in bed most of the time." The film was well-received in preview screenings, and promotions took over, with a still from the film being used in Simmons advertisements. The only group not pleased was the Mellon Institute, who did not approve of the studio mocking their study.

This was followed in 1936 by How to be a Detective. The early success of How to Sleep prompted MGM to rush two more short films featuring Benchley, How to Train a Dog, a spoof of dog-training techniques, and How to Behave, which lampooned etiquette norms. How to Sleep was named Best Short Subject at the 1935 Academy Awards, while the latter two shorts were not as well received.

Benchley returned to the cinema in 1937, cast in the revue Broadway Melody of 1938, and in his largest role to that point, the critically-panned Live, Love and Learn. A short that Benchley completed for MGM, A Night at the Movies, was Benchley's greatest success since How to Sleep, and won him a contract for more short films that would be produced in New York. These films were produced more quickly than his previous efforts (while How to Sleep needed two days, the later short How to Vote needed less than twelve hours), and took their toll on Benchley. He still completed two shoots in one day (one of which was The Courtship of the Newt), but rested for a while following the 1937 schedule.

Benchley's return yielded two more short films, and his high profile prompted negotiations for sponsorship of a Benchley radio program and numerous appearances on television shows, including the first television entertainment program ever broadcast, an untitled test program using an experimental antenna on the Empire State Building. The radio program, Melody and Madness, was more a showcase for Benchley's acting, as he did not participate in writing it. It was not well received, and was removed from the schedule.

Later life

1939 was a bad year for Benchley's career. Besides the cancellation of his radio show, Benchley learned that MGM did not plan to renew his contract, and The New Yorker, frustrated with Benchley's film career taking precedence over his theatre column, hired a new critic. Following his final New Yorker column in 1940, Benchley signed with Paramount Pictures for another series of one-reel shorts, all filmed at Paramount's Long Island studio in Astoria, New York. Most of them were adapted from his old essays ("Take the Witness!," with Benchley fantasizing about conquering a tough cross-examination, was filmed as The Witness; "The Real Public Enemies," showing the criminal tendencies of sinister household objects, was filmed as Crime Control, etc.). Benchley also received two more feature-length roles: Walt Disney's The Reluctant Dragon, in which Benchley tours the various departments of the Disney studio, and Nice Girl? with Deanna Durbin, noteworthy for a rare dramatic performance by Benchley.

Benchley's roles primarily came as a freelance actor, as his Paramount shorts contract didn't pay as well as feature films. Benchley was cast in minor roles for various romantic comedies, some shoots going better than others. He appeared in prominent roles with Fred Astaire in You'll Never Get Rich (1941) and The Sky's the Limit (1943). Paramount did not renew his contract in 1943, and Benchley signed back with MGM with an exclusive contract. The situation was not positive for Benchley, as the studio "mishandled" him and kept Benchley too busy to complete his own work. His contract concluded with only four short films completed and no chance of signing another contract. 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 in December of that year.

While Benchley's books and Paramount contract were giving him financial security, he was still unhappy with the turn his career had taken. By 1944 he was taking thankless roles in the studio's least distinguished films, like the rustic musical National Barn Dance. By this time Robert Benchley's screen image was established as a comic lecturer who tried but failed to clarify any given topic. 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.

Benchley's alcoholism, already a problem, worsened and he was diagnosed with cirrhosis of the liver. (Ironically, when younger, he had been an adamant teetotaler.) While he completed his year's work, his condition continued to deteriorate, and Benchley died in a New York hospital on November 21, 1945. His family opted for a private funeral service, and his body was cremated and interred in a family plot on the island of Nantucket.

The Algonquin Round Table was a group of New York City writers and actors who met regularly between 1919 and 1929 at the Algonquin Hotel. 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, actor Harpo Marx, and journalist/critic Heywood Broun, who gained prominence due to his positions during the Sacco and Vanzetti trial. The table gained prominence due to the media attention the members drew as well as their collective contributions to their respective areas.

Benchley's humor was molded during his time at Harvard. While his skills as an orator were already known by classmates and friends, it was not until his work at the Lampoon that his style formed. The prominent styles of humor were then "crackerbarrel," which relied on devices such as dialects and a disdain for formal education in the style of humorists such as Artemis Ward and Petroleum Vesuvius Nasby, and a more "genteel" style of humor, very literary and upper-class in nature, a style popularized by Oliver Wendell Holmes. While the two styles were, at first glance, diametrically opposed, they coexisted in magazines such as Vanity Fair and Life. The Lampoon primarily used the latter style, which suited Benchley. 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.

Benchley’s definition of humor was simplicity itself: “Anything that makes people laugh.” His favorite nursery rhyme was "One, two, three, / Buckle my shoe."

Benchley's characters were typically exaggerated representations of the common man. They were designed to create a contrast between himself and the masses, who had less common sense. The character is often befuddled by many of the actions of society and is often neurotic in a "different" way ... the character in How to Watch Football, for instance, finds it sensible for a normal fan to forgo the live experience and read the recap in the local papers. This character, labeled the "Little Man" and in some ways similar to many of Mark Twain's protagonists, was based on Benchley himself; the character did not persist in Benchley's writing past the early 1930s, but survived in his speaking and acting roles. This character was apparent in Benchley's Ivy Oration during his Harvard graduation ceremonies, and would appear throughout his career, such as during "The Treasurer's Report" in the 1920s and his work in feature films in the 1930s.

Topical, current-event style pieces written for Vanity Fair during the war did not lose their levity, either. He was not afraid to poke fun at the establishment (one piece he wrote was titled "Have You a Little German Agent in Your Home?"), and his common man observations often veered into angry rants, such as his piece "The Average Voter," where the namesake of the piece "[F]orgets what the paper said...so votes straight Republicrat ticket." 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.

In his films, the common man exaggerations continued. Much of his time in the films was spent spoofing himself, whether it was the affected nervousness of the treasurer in The Treasurer's Report or the discomfort in explaining The Sex Life of the Polyp to a women's club. Even the longer, plot-driven shorts, such as Lesson Number One, Furnace Trouble, and Stewed, Fried and Boiled, show a Benchley character overmatched by seemingly mundane tasks. Even the more stereotypical characters held these qualities, such as the incapable sportscaster Benchley played in The Sport Parade.

Benchley's humor inspired a number of later humorists and filmmakers. Dave Barry, author, onetime humor writer for the Miami Herald, and judge of the 2006 Robert Benchley Society Award for Humor, has called Benchley his "idol" and he "always wanted to write like [Benchley]." Horace Digby claimed that, "[M]ore than anyone else, Robert Benchley influenced [his] early writing style." Outsider filmmaker Sidney N. Laverents lists Benchley as an influence as well, and James Thurber used Benchley as a reference point, citing Benchley's penchant for presenting "the commonplace as remarkable" in The Secret Life of Walter Mitty.

Benchley produced over 600 essays, which were initially compiled in twelve volumes, during his writing career. He also appeared in a number of films, including 48 short treatments that he mostly wrote or co-wrote and numerous feature films.

Posthumously, Benchley's works continue to be released in books such as the 1983 Random House compilation The Best of Robert Benchley, and the 2005 collection of short films Robert Benchley and the Knights of the Algonquin, which compiled many of Benchley's popular short films from his years at Paramount with other works from fellow humorists and writers Alexander Woollcott and Donald Ogden Stewart.