lbert Hirschfeld, whose inimitable caricatures captured the appearance and personality of theater people for more than half a century, died in his sleep today in New York City. He was 99 years old.

Mr. Hirschfeld was the best-known artist in the world of theater and had won a special Tony — an Antoinette Perry award — as a sign that the theater world welcomed him not only as an observer but also as one of its own.

He was a familiar figure at first nights and at rehearsals where he had perfected the technique of making a sketch in the dark, using a system of shorthand notations that contributed to the finished product.

He continued to work and to drive his own car well into his 90's, virtually until his death. In 1996, a film documentary of the artist's life by Susan W. Dryfoos, "The Line King," rich in tributes from those he had drawn and from those he worked with, drew the comment from Nora Sayre, reviewing the movie in The New York Times: "At present he is 93, and that is the least important thing about him." The film was nominated for an Academy Award.

In that year, Mr. Hirschfeld was also named as one of six New York City Landmarks by the New York Landmarks Conservancy.

Mr. Hirschfeld was best known for the caricatures that appeared in the drama pages of The New York Times. But his work also appeared in books and other publications and is in the collections of many museums, including the Metropolitan Museum of Art, the Museum of Modern Art and the Whitney Museum of American Art in Manhattan, the Fogg Museum in Cambridge, Mass., and the museums of art in St. Louis, his hometown, and Cleveland.

His other artistic work often reflected his travels to the South Pacific and to Japan, where he was deeply influenced by esthetics and techniques.

To be the subject of a Hirschfeld drawing endowed one with a special cachet. To find the word "Nina," the name of his daughter, which was often hidden several times in the lines of his caricatures, was a weekend pastime for millions of readers.

His art was compared by critics with that of Daumier and Toulouse-Lautrec but, ultimately, it was all Hirschfeld, cannily perceptive, wittily amusing and benignly pointed.

Mr. Hirschfeld's art was distinguished by his deep feeling for people. He never went for the jugular, except on one occasion, when he did an ironic drawing of David Merrick, the producer, as a demonic Santa Claus. Mr. Merrick, to Mr. Hirschfeld's mixed reaction, liked it so much that he bought it and used it on his Christmas cards.

"The art of caricature, or rather the special branch of it that interests me, is not necessarily one of malice," the artist wrote in an introduction to his 1970 book, "The World of Hirschfeld."

"It is never my aim to destroy the play or the actor by ridicule," he continued. "The passion of personal conviction belongs to the playwright; the physical interpretation of the character belongs to the actor; the delineation in line belongs to me. My contribution is to take the character — created by the playwright and acted out by the actor — and reinvent it for the reader."

Mr. Hirschfeld's "reinventions" caught the spirit of their subjects with lines that, studied individually, might seem irrelevant but, taken together, added up to characteristic eyes, hairdos and motions — all in such a way as to distill the character of the person under study.

Ray Bolger once said he had copied the artist's conception of his appearance. Mr. Hirschfeld conceded that it was one of the phenomenons of caricature that often, in a way, the subject began to look more like the drawing than he actually looked like himself.

Barbra Streisand emerged birdlike, all points, with wide-open mouth and exotically lidded eyes. Zero Mostel, as Tevye in "Fiddler on the Roof," came across as a circle of black beard and hair with fierce eyes peering upward, as at a heaven that did not understand. Phil Silvers was all high forehead and eyeglasses, atop a small curve of a mouth.

Illustrating a 1966 production of Chekhov's "Ivanov," John Gielgud's bearded face thrusts forward, with slitted eyes and a look that conveys an impression of being very Slavic indeed. There are stars in the eyes, over the toothy grin, of President Franklin Delano Roosevelt, drawn in 1944.

Standing Out Amid the Newsprint

"Mr. Hirschfeld's style is ideally suited to the newspaper," John Russell, art critic of The Times, wrote in a review of a Hirschfeld volume. "His strong compositions and brilliant areas of texture smash into the overall gray of the newsprint page and his blacks — whether George Burns's cigar, Arthur Miller's spectacles or Emlyn Williams's eyebrows — punctuate his drawings like cymbal clashes in a Brahms overture."

"The alert reader will be able to find several actors and actresses depicted more than once and can enjoy the transformation that the actor undergoes in many roles," Mr. Russell added.

Mr. Hirschfeld cut a striking figure, a lively, white-haired, white-bearded man about 5 feet 8 inches tall, who described himself this way: "A couple of huge eyes and huge mattress of hair. Large eyes with superimposed eyebrows. No forehead. The forehead that you see is just the hair disappearing."

He was never at a loss for words or pictures; in the 1930's and 40's, he wrote pieces on comedians, actors, Greenwich Village and films for The Times. In one, he sharply criticized "Snow White," Walt Disney's animated movie, for imitating "pantographically" factual photography and for being in the "oopsy-woopsy school of art practiced mostly by etchers who portray dogs with cute sayings."

His own finished products were completed mostly on the drawing board next to the barber's chair he used while working in the Manhattan brownstone in the East 90's that he shared with his wife, the actress Dolly Haas.

Enchanted by Line On a Trip to Bali

His caricatures began in his mind's eye, and it was only as he limned them on paper that the lines juxtaposed into the pictures he had conceived. Some editors with photographically literal minds occasionally found his artistic flights of fancy too outspoken for their own tastes, but they rarely interfered with his freedom to interpret as he saw fit.

The Hirschfeld story began on June 21, 1903, when he was born in St. Louis, one of three sons of Isaac and Rebecca Hirschfeld.

When he was 12 years old and had already started art lessons, the family moved to New York City. He attended public schools and the Art Students League. At 16, he worked as an office boy. Two years later he became an art director for David O. Selznick, the motion-picture producer, and then moved to Warner Brothers. In 1924, he went to Paris where he continued his studies in painting, sculpture and drawing.

It was during a trip to Bali — where the intense sun bleached out all color and reduced people to "walking line drawings," as he later recalled — that he became "enchanted with line" and concentrated on that technique.

Doodling a Sketch In the Dark

While on a visit to New York in 1926 from Paris, he went to the theater one evening with Richard Maney, a theatrical press agent who was handling his first show, a production that starred Sacha Guitry, the French star, in his first American performance.

With a pencil, Mr. Hirschfeld doodled a sketch in the dark on his program. Mr. Maney liked it and asked Mr. Hirschfeld to repeat it on a clean piece of paper that could be placed in a newspaper. It appeared on the front page of The New York Herald-Tribune, which gave him more assignments. These were followed by orders from other papers. Alexander Woolcott, the drama critic who was then at The New York World, asked for some Hirschfeld drawings, starting with one of himself.

Some weeks later, the artist received a telegram from Sam Zolotow of The Times's drama department asking for a drawing of Harry Lauder, who was making one of his numerous farewell appearances. Mr. Hirschfeld delivered it to the messenger desk at the newspaper. A few weeks later, he had another assignment from The Times and gave the result to the desk once again.

This went on for about two years, he later recalled, until he first met Mr. Zolotow in a theater lobby. He was told to deliver his next drawing in person and he did, making the acquaintance of Brooks Atkinson, then The Times's drama critic, who became a close friend.

Lester Markel, the Sunday editor of The Times, suggested that Mr. Hirschfeld work exclusively in the field of theater for the newspaper. The artist welcomed the arrangement because he felt it gave him greater freedom. The custom elsewhere was for the producer of the show to pay for the drawings, but The Times paid the artist directly. Mr. Hirschfeld never was a salaried employee of The Times but worked on a freelance basis that left ownership of his work in his hands after it had been published in the newspaper.

Closer to Groucho Than to Karl Marx

He applied his art to other subjects elsewhere. In the 1920's and early 30's, imbued with a sense of social concern, Mr. Hirschfeld did serious lithographs that appeared, for no fee, in The New Masses, a Communist-line magazine. Eventually, he realized that the magazine's interest was politics rather than art.

After a dispute about a caricature he had made of Father Charles E. Coughlin, the right-wing, anti-Semitic radio priest, the artist renounced a political approach to his work and, in his book, "The World of Hirschfeld," later wrote, "I have ever since been closer to Groucho Marx than to Karl."

Although his work for the newspaper was in black and white, he worked in color for such publications as American Mercury magazine, for which he drew many covers.

The Hirschfelds' daughter, Nina, was born in 1945. On Nov. 5 of that year, her name made its debut in the pages of The Times's Sunday edition, on an imagined poster in a circus scene for a drawing about a new musical, "Are You With It?" The world may have lost track of the show but it kept up with Nina, a name covertly insinuated into a caricature several times — perhaps in the fold of a dress, a kink of hair, the bend of an arm.

So popular did the Ninas become that the military used them in the training of bomber pilots to spot targets. A Department of Defense consultant found them useful in the study of camouflage techniques.

The Number of Ninas? Look in the Lower Right

Mr. Hirschfeld realized how addicted readers had become to Ninas when he purposely omitted them one Sunday only to be besieged by complaints from frustrated Nina hunters.

One Nina fan was Arthur Hays Sulzberger, then the publisher of The Times. In 1960 he wrote a letter to Mr. Hirschfeld to say that he always first looked for Ninas in Hirschfeld drawings but had learned that each included more than one.

"That really isn't fair, since not knowing how many there are leaves one with a sense of frustration," Mr. Sulzberger wrote.

A letter from another reader suggested that the artist note in the caricature how many times a Nina appeared. From that time on, Mr. Hirschfeld appended the number of Ninas in the lower right-hand corner of each drawing.

Mr. Hirschfeld believed that acceptance of caricatures was a slow process and one that was always difficult for the artist. Occasionally, actors and producers hinted at lawsuits or withdrawal of advertising because they did not find his drawings sufficiently attractive.

But his art flourished and endured and, indeed, it sometimes seemed as though there were Hirschfelds at every point of the compass. He was represented for more than a quarter of a century by the Margo Feiden Galleries, which once estimated that there were more than 7,000 Hirschfeld originals in existence. One that is no longer in existence is a Hirschfeld self-portrait reproduced in paint on Madison Avenue between 62d and 63d Streets, in front of the gallery in 1994. It was 48 feet long, complete with Ninas, and survived a partial washout by rain the first day.

If you couldn't join Hirschfeld, you could lick him. In 1991 the United States Postal Service issued a booklet of five 29-cent stamps honoring comedians — Stan Laurel and Oliver Hardy, Edgar Bergen and Charlie McCarthy, Jack Benny, Fanny Brice and Bud Abbott and Lou Costello — as designed by the artist; contrary to post office policy forbidding secret marks, he was allowed to insert his trademark Ninas into the depictions. He also did the drawings for other stamps representing Lon Chaney, Clara Bow, Charlie Chaplin, Harold Lloyd, the Keystone Kops and Rudolf Valentino. In 1987, Mr. Hirschfeld's caricature of Trygve Lie, first Secretary General of the United Nations, went on a cover issued by the World Federation of United Nations Associations.

Travel Books With S. J. Perelman

In the early 1940's, he and a friend, the writer S. J. Perelman, collaborated on a musical with Ogden Nash and Vernon Duke. It was called "Sweet Bye and Bye" and opened and closed in Philadelphia on the same night without ever reaching Broadway.

"We had to leave the country after that," Mr. Hirschfeld later said.

Subsequent travels resulted in such books — words by Perelman, pictures by Hirschfeld — as "Westward Ha! or Around the World in 80 Clichés" and "Swiss Family Perelman."

Mr. Hirschfeld wrote several books by himself, including "Show Business Is No Business" (reissued in 1983), "The American Theater as Seen by Hirschfeld," the autobiographical "The World of Hirschfeld"and "Show Business Is No Business: Hirschfeld's World and Art and Recollections From Eight Decades."

In 1995, he was enshrined in the on-line age by a CD-ROM, "Hirschfeld: The Great Entertainers." He received more honors and awards than perhaps any other living American artist. He received a special Tony award in 1975 and was the first recipient, in 1984, of the Brooks Atkinson Award, bestowed on him by the League of New York Theaters and Producers and the American Theater Wing.

Dolly Haas Hirschfeld, who was his wife, adviser and social director for 52 years, died in 1994. An earlier marriage to Florence Ruth Hobby ended in divorce. In 1996 he married Louise Kerz, a research historian in the arts and a longtime friend, who survives him. He is also survived by his daughter and a grandson, Matthew.

In something of a self-critique, Mr. Hirschfeld, in a letter to The Times in 1986, expressed his opinion about an article in the Science section on defining beauty. "Beauty is incapable of being defined scientifically or esthetically," he wrote. "Anarchy takes over. Having devoted a long life to the art of caricature I have rarely convinced anyone that caricature and beauty are synonymous. Beauty may be the limited proportions of a classic Greek sculptured figure but it does not have to be — it could be an ashcan."