He was the inspiration for Sheridan Whiteside, the main character in the play The Man Who Came to Dinner by George S. Kaufman and Moss Hart, and for the far less likable character Waldo Lydecker in the classic film Laura. He claimed to be the inspiration for Rex Stout's brilliant detective Nero Wolfe, but Stout, although he was friendly to Woollcott, said there was nothing to this idea.
Woollcott's review of the Marx Brothers' Broadway debut, I'll Say She Is, helped highlight the renaissance of the group's career and started a life-long friendship with Harpo Marx. Harpo's two adopted sons, William (Bill) Woollcott Marx and Alexander Marx, are named after Woollcott.
Woollcott was born in an 85-room house, a vast ramshackle building that had once been a commune. It was called The North American Phalanx, and was in Phalanx, New Jersey. There were many social experiments in the mid-1800s, some more successful than others. When The Phalanx fell apart after a fire there in 1854, it was taken over by the Bucklin family, Woollcott's maternal grandparents. There, amid his extended family, Woollcott spent large portions of his childhood. His father was a ne'er-do-well Cockney who drifted through various jobs, sometimes spending long periods away from his wife and children. Poverty was always close at hand.
The Bucklins and Woollcotts were avid readers, giving young Aleck a lifelong love of literature, especially the works of Charles Dickens. Through a family friend, Dr. Alexander Humphreys (after whom he was named), Woollcott made his way through college, graduating from Hamilton College, in upstate New York, in 1909. There, 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.
He was one of the most prolific drama critics at The New York Times and was an owlish character whose caustic wit either joyously attracted or vehemently repelled the artistic communities of 1920s Manhattan. He was banned for a time from reviewing certain Broadway theater shows. As a result he sued the Shubert theater organization for violation of the New York Civil Rights Act, but lost in the state's highest court in 1916 on the grounds that only discrimination on the basis of race, creed or color was unlawful. From 1929 to 1934 Woollcott wrote a column called "Shouts and Murmurs" for The New Yorker. He was frequently criticized for his ornate, florid style of writing and, in contrast to his contemporaries James Thurber and S. J. Perelman, he is little read today, although his book, While Rome Burns, published by Grosset & Dunlap in 1934, was in 1954 named by critic Vincent Starrett as one of the 52 "Best Loved Books of the Twentieth Century".
He was one of the most-quoted men of his generation. Among Woollcott's classics is his description of the Los Angeles area as "Seven suburbs in search of a city" — a quip often attributed to his friend Dorothy Parker. Describing The New Yorker editor Harold Ross, he said: "He looks like a dishonest Abe Lincoln."
Woollcott, who claimed the Brandy Alexander was a concoction named after him, was known for his savage wit. He once said about another contemporary wit and piano player: "There is absolutely nothing wrong with Oscar Levant that a miracle can't fix." He also was known to greet friends with, "Hello, Repulsive." Famously, he published the shortest theatrical review in history by submitting to his editor simply: "Ouch."
His judgments were frequently eccentric. Dorothy Parker once said: "I remember hearing Woollcott say reading Proust is like lying in someone else's dirty bath water. And then he'd go into ecstasy about something called, Valiant Is the Word for Carrie, and I knew I had enough of the Round Table."
After being kicked out of the apartment he shared with The New Yorker founders Harold Ross and his wife Jane Grant, Woollcott moved first into the Hotel des Artistes on the Upper West Side of Manhattan, then to an apartment at the far end of East 52nd Street. The members of the Algonquin Round Table had a debate as to what to call his new home. Franklin P. Adams suggested that he name it after the Indian word "Ocowoica", meaning "The-Little-Apartment-On-The-East-River-That-It-Is-Difficult-To-Find-A-Taxicab-Near". But Dorothy Parker came up with the definitive name: Wit's End.
Woollcott yearned to be as creative as the people with whom he surrounded himself. Among many other endeavors, he tried his hand at acting and co-wrote two Broadway shows with playwright George S. Kaufman, while appearing in two others. He also starred as Sheridan Whiteside, for whom he was the inspiration, in the traveling production of The Man Who Came to Dinner in 1940. He also appeared in several cameos in films in the late 1930s and 1940s.
Politically, Woollcott called for normalization of U.S.-Soviet relations. He was a friend of reporter Walter Duranty, even though he described him as a "man from mars". and Soviet foreign minister Maxim Litvinov, and traveled to the USSR in the 1930s, as well as sending his friend Harpo Marx to Moscow on a comedy tour in 1934. Yet he was attacked viciously in the left-wing press after his visit to the Soviet Union for his less than laudatory depiction of the "worker's paradise." Towards the end of Woollcott's life he semi-retired to Neshobe Island in Lake Bomoseen in Vermont, which he had purchased.
On January 23, 1943, Woollcott appeared on his last radio broadcast, as a participant in a panel discussion on the CBS Radio program The People's Platform. Marking the tenth anniversary of Adolf Hitler's rise to power, the subject was "Is Germany Incurable", and featured Woollcott and Rex Stout and Marcia Davenport. Ten minutes into the broadcast, Woollcott commented that he was feeling ill, but continued his remarks. "It's a fallacy to think that Hitler was the cause of the world's present woes," he said. Woollcott continued, adding "Germany was the cause of Hitler. He said nothing further. The radio audience was unaware that Woollcott had suffered a heart attack. He died at New York's Roosevelt Hospital a few hours later, aged 56.
He was buried in Clinton, New York, at his alma mater, Hamilton College, but not without some confusion. By mistake, his ashes were sent to Colgate University in Hamilton, New York. When the error was corrected and the ashes were forwarded to Hamilton College, they arrived with 67¢ postage due.