Mrs. Roosevelt knew about Woollcott’s high-handed ways (years later she described him as one of the White House’s most “peculiar” guests), yet she invited him to the White House several times.⁶ Clearly, she enjoyed his company. She may also have recognized that they had much in common. Both were conveners—people who brought other people together. Both were enthusiastic promoters of causes and individuals. Both were avid theatergoers. Both were accomplished lecturers and radio performers with large national followings. Both hated to be alone. Most important, both were high-energy people who thrived on hard work.

Physically they could not have looked more dissimilar. While Mrs. Roosevelt was tall and lanky, Woollcott was short and fat. With his large head, dense horn-rimmed glasses, little beak-shaped nose, twitching mustache, and flowing chins, Woollcott resembled a large ruffled owl, or as his friend, Harpo Marx, once said, “something that had gotten loose from Macy’s Thanksgiving Day parade.” His voice was “very high and very light” and he had “a kind of pompousness in his walk,” recalled Janet Fox Goldsmith, an actress who worked with Woollcott; “he was kind of a little king.”⁷

Woollcott‘s “kingdom” consisted of his friends to whom he was both generous and loyal. There was a caveat to his friendship, however. “Everyone . . . he cared about had to have some degree of success or had to have some quality in his opinion that was admirable . . . worthy of talking about,” said his physician and protégé Dr. Frode jensen. A confirmed name-dropper, Woollcott regarded Franklin and Eleanor Roosevelt as two of his more illustrious friends in a gallery that by 1937 included such luminaries as Dorothy Parker, Robert Benchley, Ring Lardner, George S. Kaufman, Moss Hart, Noel Coward, Lynn Fontanne, Alfred Lunt, and Talullah Bankhead.⁸

Woollcott first came to the White House in January 1937 when he attended one of the Roosevelts’ Sunday scrambled eggs suppers. At the time he was touring in a play called Wine of Choice and already a national figure, he was well known for his lecture tours and his CBS radio program on which he discussed books, the theater, crime stories, his famous friends, and his pet causes. Among those causes had been FDR’s 1936 reelection.⁹ Three months later, he spoke at a White House dinner honoring his friend Broadway actress, Katharine Cornell, who received the Chi Omega National Achievement award for her work in the theater (Eleanor Roosevelt was a member of the group’s nominating committee). Later that year, he served on a committee of “book connoisseurs” who recommended a list of five hundred books for the White House library.¹⁰

In July 1939, Woollcott stayed with the Roosevelts at Hyde Park. In her syndicated column, “My Day,” Eleanor Roosevelt confessed that she felt “a little nervous for fear that Mr. Woollcott would not enjoy eating his meals out of doors.” The Roosevelts loved to picnic, and happily she found that “he prefers that to being indoors.” She also hit upon one of Woollcott’s most endearing traits as a guest or host. He was “a delightful story teller” whose “fund of tales” was “endless and always . . . interesting.”¹¹

Of the two Roosevelts, Woollcott was closer to the First Lady. Although he shared with the president a delight in detective stories and the novels of Charles Dickens, their relationship was not warm. Their mutual coolness may have stemmed from the fact that both were accustomed to dominating any room they entered. “When he was in Mr. Roosevelt’s company, Aleck behaved rather like a small child,” wrote his biographer Howard Teichmann. “Either he maintained a pouting silence or he spoke too eagerly, too pleasingly, and too loudly.”¹² Around Mrs. Roosevelt, however, Woollcott assumed the attitude of an attentive cavalier. He offered to run errands for her, advised her on what books and films to read and see, and on one occasion reviewed radio scripts for her. He often signed his letters to her, “Yours to command.”¹³ For her part, Mrs. Roosevelt not only enjoyed Woollcott’s company but also publicized his work in “My Day.” For example, in December 1937 when her cousins, Alice Roosevelt Longworth and Theodore Roosevelt Jr., published an anthology of poetry, she noted that Woollcott had originated the project by asking his radio listeners to send them “anything they had read and clipped out and put into a drawer to read again.” In February 1940, she recommended “three stories about dogs” Woollcott had written: “Everyone who likes dogs will enjoy these stories.”¹⁴

In the spring of 1940, Eleanor Roosevelt and Woollcott met in San Francisco. She was there to give a lecture, while he was touring in a production of the hit play, The Man Who Came to Dinner. Woollcott invited her to have coffee with him in his sumptuous suite at the Fairmont Hotel, an event she described as “one of my most pleasant San Francisco experiences.” She reciprocated by inviting him to stay at the White House during the play’s Washington run. Her invitation turned out to be a case of life imitating art.¹⁵

In 1938, Woollcott, then touring a play that he considered badly written, had asked his friend Broadway playwright, Moss Hart, and Hart’s partner, George S. Kaufman, to write a play for him. Kaufman and Hart, who had experienced Woollcott’s dictatorial ways firsthand, took his manners and his mannerisms as their starting point. Then they asked themselves, what if their friend had become ill while staying at someone’s house and had had to stay on indefinitely?¹⁶

The result was The Man Who Came to Dinner, which opened on Broadway in the fall of 1939. The play’s plot revolves around the character of Sheridan Whiteside, a popular lecturer, who finds himself trapped in the home of a prominent Mesalia, Ohio couple after falling and fracturing his hip on their doorstep. He returns the hospitality of his reluctant host and hostess by turning their lives upside down. Although he is wheelchair bound, he commandeers the first floor of the house as well as the domestic staff and then proceeds to run up huge bills telephoning or cabling his famous friends all over the world. Some of those friends, including thinly disguised versions of Harpo Marx and Noel Coward, actually turn up in Mesalia, where they add to the fun and mayhem. He also encourages the children of the family to follow their dreams while trying to thwart a budding romance between his secretary and the local newspaper editor.¹⁷

Although Woollcott loved the play, he ultimately decided not to star in the Broadway production in case it flopped. He hid his anxiety behind his customary bravado. “It struck me that it would be alienating and even offensive for me to come forward and say in effect, ‘See how rude and eccentric I can afford to be,’” he wrote his British friend, Lady Sibyl Colefax. “Besides I had a sneaking notion that the play would be a success, in which case I might have to stay in New York for two years. . . . However, I thought the play very funny and told George Kaufman that once the joke had been sprung I would not at all mind heading a second company.”¹⁸

The play was a huge hit, and Woollcott’s wish came true. He headlined a West Coast touring production of The Man Who Came to Dinner that opened in Santa Barbara, California, on February 9, 1940 and moved up the coast to San Francisco. Shortly after Woollcott had coffee with Eleanor Roosevelt, however, he suffered a massive heart attack and had to cancel the tour.¹⁹ She wrote him that she was “very much distressed to read in the newspapers” that he was ill and “had to give up the play. I do hope you will get rest and take care of yourself.”²⁰ While recuperating at his Vermont retreat that fall, Woollcott wrote Mrs. Roosevelt inviting her to visit—a recurring topic in their subsequent correspondence. She declined the invitation, but she did not forget Woollcott. By November, he was well enough to endorse FDR’s third term bid on a radio broadcast he paid for himself, and by December, he was back at the White House.²¹

In his usual high-handed manner, Woollcott had asked to bring his secretary with him as he was “in arrears” with his work. Eleanor Roosevelt complied with this request, writing Woollcott, “I hope you will bring your secy & make yourself at home.” She then directed that he be put “in large N.E. room [S.E.?]—secy in small room.”²² Ever the curmudgeon, Woollcott found his accommodations less than desirable, mostly because of the presence of other White House guests. Writing to George Kaufman, he said, “This place isn’t what it used to be. My room is a vast, comfortable place where the Emancipation Proclamation was signed and where later the king of England [George VI] was lodged.” But, he reported, since the journalist Martha Gellhorn—(who had only a month before married author Ernest Hemingway)—was leaving and his bête noire, the novelist-playwright Edna Ferber was moving in, “I will be back at the Gotham [Hotel] tomorrow evening.”²³

No hint of Woollcott’s distress permeated Eleanor Roosevelt’s “My Day” column. Instead, she told readers about the way Woollcott “gathered” her and her other guests to listen to a poignant radio broadcast between Emlyn Williams, author of the play The Corn Is Green, then enduring the Blitz in England, and the New York cast of the play, which included his wife, the actress Molly Shan. In the same column, she also slyly alluded to The Man Who Came to Dinner when she compared Woollcott to his alter ego Sheridan Whiteside and hinted at his future visit. “Though I know he fancies himself in that particular role,” she wrote, “as his hostess, I will have to say that in real life he is far from . . . the character which is depicted on the stage. We have enjoyed every minute of his visit and the latchstring hangs out for the future.”²⁴

Woollcott’s subsequent arrival with the company of The Man Who Came to Dinner in February 1941 was a major event. “A Prodigious Fellow Arrives Tomorrow Night,” said the headline of the February 23 Washington Post over a story detailing Woollcott’s multiple careers. Eleanor Roosevelt also plugged his arrival in “My Day,” noting that he and his secretary were “settled in their rooms, prepared to meet all the rigors of daily acting.” Wise to his ways and perhaps fearing that the stress of playing Sheridan Whiteside every night would affect his behavior at the White House, she acknowledged that “if one incurred his displeasure, the imp in ‘The Man Who Came to Dinner’ might conceivably come forth even in my most welcome guest.” At least initially, however, Woollcott was on his best behavior, bringing films made in Florida and Vermont for Mrs. Roosevelt and her other guests to view.²⁵

That said, Woollcott wasted no time in making himself thoroughly at home. Writing George Kaufman’s wife, Beatrice, on February 25, he suggested that, “any of your party could pay a morning call on me in our quarters here [he was ensconced in the Rose Bedroom] on Saturday or Sunday or both.” He cautioned her, however, that “if you have any notion of visiting the tenants of this house . . . you should write Mrs. Roosevelt announcing that you are coming to town, reporting where you will be lodged and asking if there is any time when you can pay your respects.”²⁶

That night the Roosevelts went to see Woollcott at the National Theatre, a rare outing for FDR, who seldom went to the theater. Eleanor Roosevelt told readers of “My Day” that the occasion “was one of the few times I have ever seen the National Theatre packed, no empty seats were to be seen.” Of Woollcott’s performance, she said, “His appearance adds greatly to the flavor of the scenes.”²⁷ She also noted that some of the play’s lines had been changed. For example, when Sheridan Whiteside urges June, the daughter of his upper-middle-class hosts, to marry a labor organizer who is organizing her father’s factory, and June says, “You—You mean that, Mr. Whiteside?” Whiteside/Woollcott replied, “No, marry Hamilton Fish” (the isolationist Republican congressman Hamilton Fish Jr., who represented the Roosevelts’ Hyde Park congressional district). On a more poignant note, Whiteside’s Christmas Day telephone call came from Walt Disney rather than from the writer Gertrude Stein as originally written, in tacit recognition of the fact the Nazis then occupied Paris. However, Whiteside’s oblique reference to Eleanor Roosevelt’s legendary hospitality in the form of the “twenty-two Chinese students who came straight from the White House” to see him remained as written.²⁸

After the performance, Woollcott told a reporter that he hoped he would finish out his stay at the White House and not “get put out beforehand.” Then he and the rest of the cast members repaired to the White House for supper.²⁹ “Supper was served in the State Dining Room,” recalled Janet Fox Goldsmith, who played Whiteside/Woollcott’s nurse in the play. “It was marvelous and we all enjoyed ourselves thoroughly.” However, Woollcott, never one to settle for moderation when excess would do, continued to host midnight suppers after each night’s performance “and word came back to us that the Roosevelts were getting a bit upset. . . . The White House chef gave his notice saying, ‘I’ve served an awful lot of people but at two in the morning?’”³⁰ Woollcott’s active social life particularly annoyed White House Chief Usher, Howell G. Crim, who could not get over the way the actor invited “guests right up to his room.” Crim also found Woollcott’s habit of ringing for coffee “at all hours of the night” irritating.³¹

As his visit drew to a close, Woollcott wrote a vacationing Eleanor Roosevelt in Florida, using White House notepaper because “I thought you would get a thrill out of receiving a letter written on this stationery.” After telling her about a snowfall in Washington that “flabbergasted” the city, he described FDR’s reaction to Woollcott’s airy dismissal of the fact that the bad weather would reduce the size of his audience. “I replied cheerfully that inasmuch as the seats had all been sold I would be undisturbed by the fact that the people did not occupy them. He [FDR] seemed decently appalled at so commercial a viewpoint.”³²

Woollcott finally left the White House on March 9, 1941, when the Washington run of The Man Who Came to Dinner ended. He never again spent so much time at the White House, but he did visit several times in 1942. Although he generally managed to behave, there were times when “the imp” of The Man Who Came to Dinner reappeared. For example, he never overcame his habit of demanding coffee at all hours of the day and night. His demands plus the coffee rationing World War II brought on caused “a strain,” according to the White House housekeeper, Henrietta Nesbitt. Woollcott, whose health was failing, was so “irascible and impatient,” she recalled, that the staff who worked on the Second Floor “was afraid of his sharp tongue.” He did, however, leaven his demands with humor “so they couldn’t resent him.”³³

On at least two occasions, Woollcott shifted from guest to host, a shift that was easy to accomplish as Mrs. Roosevelt was often away from the White House. At one point he met her as she was coming in and he was going out. “Welcome, Mrs. Roosevelt, come right in,” he said. “I am delighted to see you. Make yourself at home.”³⁴ Another time he actually extended White House hospitality to a young friend serving in the Marines. When, after a night of eating and drinking with Woollcott and his friend, the writer Thornton Wilder, the young man missed the last train back to his barracks, Woollcott—in a manner Sheridan Whiteside would have envied—took him back to the Executive Mansion and “not finding so much as a third-assistant usher on duty” installed the startled serviceman in a room once used by Winston Churchill. By way of apology, he wrote to Mrs. Roosevelt, who was then at Hyde Park, that it was not true “that as soon as you and the President had carelessly left the premises unguarded, I quartered a regiment of marines at the White House.”³⁵

Despite his White House peccadilloes, Eleanor Roosevelt and Woollcott continued to stay in touch. They met one last time in New York City, shortly before his sudden death on January 23, 1943. According to “My Day,” they discussed “the last war and this one, our mistakes in between, what we must to do obviate their repetition and what he himself was trying to do.” Apparently, they also discussed how she should answer when asked, “What is your war work?”—a question she apparently found “embarrassing.”³⁶ They also discussed the possibility of the first lady giving a birthday party for Woollcott. He advised her “to give the whole thing up” because “none of us has a right to plan such an evening in these times.” She reluctantly agreed.³⁷

After his death, Eleanor Roosevelt eulogized Woollcott in “My Day,” remembering his “foibles and eccentricities,” his storytelling ability, his conversational skills, and, somewhat surprisingly given his reputation for insulting friends and foes, his ability to listen, especially to young people. “I am glad to have the memory of his friendship,” she concluded. “I shall miss him.”³⁸

Eleanor Roosevelt did more than miss the man journalist Elmer Davis once called a “cross between Nero and St. Francis.” She burnished his reputation, meeting with one of his early biographers and commenting favorably when she received advance copies of his last posthumously published book, a literary anthology for servicemen called As You Were.³⁹ She also continued to remember Woollcott long after his death. More than twenty years after their meeting at the Fairmont Hotel in San Francisco, she was still reminiscing about him. “I never go there without thinking of Alexander Woollcott who used to love to stay in one of the rooms . . . where he would ask friends to come to tea,” she wrote in “My Day.” “I remember what a pleasure it was to sit and listen to him talk.”⁴⁰