Alexander Humphreys Woollcott (January 19, 1887 – January 23, 1943) was an American drama critic for The New York Times and The New York Herald, critic and commentator for The New Yorker magazine, a member of the Algonquin Round Table, an occasional actor and playwright, and a prominent radio personality.

Woollcott was the inspiration for two fictional characters. The first was Sheridan Whiteside, the caustic and malingering house-guest in the comedic play The Man Who Came to Dinner (1939) by George S. Kaufman and Moss Hart, later made into a film in 1942. The second was the snobbish and vitriolic columnist Waldo Lydecker in the novel Laura, later made into a film in 1944 in which Lydecker was played by Clifton Webb.

Woollcott was convinced he was the inspiration for his friend Rex Stout's brilliant but eccentric and very portly detective Nero Wolfe, which Stout denied.

Alexander Humphreys Woollcott was the youngest of five children of Walter and Frances (Bucklin) Woollcott, born on January 19, 1887. The family lived in an 85-room house, a vast ramshackle building in Colts Neck Township, New Jersey known as "the North American Phalanx," which had once been a commune where many social experiments were carried out in the mid-19th century. When the Phalanx fell apart after a fire in 1854, it was taken over by and became the family seat of the Bucklin family, Woollcott's maternal grandparents.

In 1889, the itinerant and often absentee Walter Woollcott moved his family to Kansas City, Missouri. The Woollcotts lived in an upscale neighborhood where, at the age of four, Alexander portrayed the character of Puck from A Midsummer Night's Dream in a tableau vivant before an audience of more than 100 at the Woollcott home. The six years Woollcott lived in Kansas City were transformative, and set him on the literary and theatrical path that would guide the rest of his life. His second-grade teacher, Sophie Rosenberger, who would remain a lifelong friend, considered him precocious and set him on a reading program that began with Louisa May Alcott and progressed to Charles Dickens by the time he was 8 years old. It was also in Kansas City that he experienced his first theatrical performance, Sinbad the Sailor. He was accompanied by his neighbor, Kansas City Times columnist Roswell Field, brother of famed author Eugene Field. When young Aleck discovered that journalists could get free tickets to theatrical events he decided that he, too would become a newspaper man.

In 1895 Walter Woollcott lost the longest job he'd ever held, and sent his wife Frances and their children back to the Phalanx, where Alexander went to school and spent most of the remainder of his boyhood. He occasionally lodged in homes in Germantown, Philadelphia and attended the Germantown Combined Grammar School, and then Central High School in Philadelphia. He had very few friends during this period and did not enjoy this chapter of his life, with the exception of summers and any time that he could get back to the Phalanx.

With the help of a family friend, he made his way through college, graduating from Hamilton College, New York, in 1909. Despite a rather poor reputation (his nickname was "Putrid"), he founded a drama group, edited the student literary magazine, and was accepted by a fraternity (Theta Delta Chi).^{[citation needed]}

Woollcott joined the staff of The New York Times as a cub reporter in 1909. In 1914, he was named drama critic and held the post until 1922, with a break for service during World War I. In April 1917, the day after war was declared, Woollcott volunteered as a private in the medical corps. Posted overseas, Woollcott was a sergeant when the intelligence section of the American Expeditionary Forces selected him and a half-dozen other newspaper men to create the Stars and Stripes, an official newspaper to bolster troop morale. As chief reporter for the Stars and Stripes, Woollcott was a member of the team that formed its editorial board. These included Harold Ross, founder of The New Yorker magazine; Cyrus Baldridge, multifaceted illustrator, author and writer; and the future columnist and radio personality, Franklin P. Adams. Going beyond simple propaganda, Woollcott and his colleagues reported the horrors of the Great War from the point of view of the common soldier. After the war he returned to The New York Times, then transferred to The New York Herald in 1922 and to The World in 1923. He remained there until 1928.