“Self-pity—it’s the only pity that counts.”
—Oscar Levant

The dazzling and self-destructive genius Oscar Levant blazed through five different careers before dying in 1972 at the age of 65. First, he was a classically trained composer, songwriter, and pianist. As a performer, he was considered the foremost interpreter of his friend George Gershwin’s concert music. Levant was an in-demand radio personality and a Hollywood actor, known for his acerbic wit and impromptu musical performances. You’ve seen him in An American in Paris, Humoresque, and The Band Wagon. He played himself in the 1945 George Gershwin biopic, Rhapsody in Blue. Finally, Levant was the best-selling author of Memoirs of an Amnesiac and, late in his abbreviated life, a coveted TV personality. Though he’s all but forgotten now—he survives mostly as a topic for pop-culture connoisseurs—at one time Levant was so recognizable that his home in Beverly Hills was a popular stop on all the Hollywood movie-stars bus tours.

This year, however, Oscar is making a comeback. He has a cameo in the new season of The Marvelous Mrs. Maisel, where he is played by Leonid Citer as a wisecracking contestant on a television game show. And he’s the subject of Good Night, Oscar, a new play by Doug Wright (who won the 2004 Pulitzer Prize for I Am My Own Wife), which opens March 12 at the Goodman Theatre in Chicago with Sean Hayes (Will & Grace) as Oscar.

Wright’s play takes place during the legendary night in November 1958 when Levant emerged from years of breakdowns, concert cancellations, and psychiatric hospitalizations to appear on The Jack Paar Show. It made television history.

Many who were on the receiving end of Oscar’s withering wit wore his jibes and insults like a badge of honor. “I knew Doris Day before she became a virgin” was a remark the singer delighted in for decades. About the actress Joan Collins, whom the movies kept scantily clad but who always wore her hair in bangs, Levant quipped, “I have now seen every part of Joan’s anatomy except her forehead!” To the popular songwriter Vernon Duke (“April in Paris”), who also composed concert music under his given name, Vladimir Dukelsky, Oscar asked, “For a man who’s destined for obscurity, why do you need two names?” Even George Gershwin, whom Oscar idolized, was not immune; he described Porgy and Bess as “a glorious paean to American Jewish music.” (George was not amused.)

But by the time of his appearance on Paar’s show, Oscar was well on his way to becoming a Hollywood recluse almost as celebrated as Howard Hughes. Paar, a friend of Oscar’s, often closed his shows by saying, “Good night, Oscar Levant, wherever you are.” He hoped to lure the pianist out of self-imposed exile. He also knew he would make great television.

Paar’s hunch was right. Oscar’s appearance created an extraordinary half-hour of television. Seated next to Paar and furiously puffing on a cigarette, Oscar lacked the groomed, unctuous aura of sincerity that marked the usual television guest. “I’m in the middle of a breakdown,” he told Paar, to a spate of nervous laughter from the audience. “It’s my fifth in two years.” When Paar noticed that Levant’s pianist’s hands were trembling, Oscar responded, “What is this?,” staring down at them as if they belonged to someone else. “And I’m supposed to do surgery!” More audience laughter.

On the subject of well-known decouplings, such as Eddie Fisher’s leaving Debbie Reynolds for Elizabeth Taylor, Oscar said, “Eddie left Debbie for Elizabeth? How high can you stoop?” And when the subject of Joe DiMaggio’s recent divorce from Marilyn Monroe came up, Oscar commiserated with DiMaggio: “No man can excel at two national pastimes.”

Nothing seemed to delight the studio audience more, though, than Oscar’s recitation of his Walpurgisnacht experiences as a mental patient. “I was thrown out of one mental hospital because I depressed the patients,” he said. “There is a fine line between genius and insanity, and I have erased that line.” That appearance was a watershed—mental illness had certainly been a theme in plays and movies, but not in real life, in prime time, in the heart of America’s most cheerfully conformist decade.

But the response to Oscar’s appearance was not all laughter. By the next morning, Paar was being criticized for exploiting mental illness, though hailed by others for the show’s bracing courage.

Oscar would have another crack at television with his own very local and bare-bones program, The Oscar Levant Show, which aired from 1958 to 1960. In a tiny studio at KCOP, in Los Angeles, it was co-hosted by Oscar’s wife, June, who sat beatifically beside him at a desk whenever he wasn’t at the piano. Paraded before a minuscule audience were guests Levant knew and admired, a jumble sale of eccentrically matched talent and genius: Christopher Isherwood and Jerry Lewis (reciting T. S. Eliot’s “The Waste Land” in a prissy falsetto); Aldous Huxley (talking up LSD) and Linus Pauling (waltzing with June); Eddie Cantor and Jack Dempsey; Irish playwright Brendan Behan and William O. Douglas—even Levant’s own psychiatrist.

Occasionally, Oscar would get thrown off the air, once for insulting his sponsor, another time for commenting on Marilyn Monroe’s marriage by a rabbi to Arthur Miller: “Now that Marilyn Monroe is kosher, Arthur Miller can eat her.”

“I didn’t mean that way,” he later protested. But it was too little, too late.

Fred Astaire’s first television appearance was on The Oscar Levant Show. Perched on a bar stool brought in from the Levant home, the surprisingly shy performer sang and reminisced for an hour with Oscar, his co-star in The Band Wagon and The Barkleys of Broadway. Remarkably, the Astaire appearance is from one of only two Levant shows to have survived.

But here’s the kicker—for much of the show’s tenure, Oscar was confined to the psychiatric ward of Mount Sinai in Los Angeles. As airtime approached, Levant’s young producer, Al Burton (Mary Hartman, Mary Hartman), would check Oscar out of the psych ward and drive him to the studio for 90 minutes of live TV, then sign him back into the hospital. It was reality television at its most real.

The day of Levant’s death, Candice Bergen had come to North Roxbury Drive to follow up on an earlier interview with Oscar, for Esquire. When Bergen arrived at the house, June, who was just leaving, told her that Oscar was upstairs resting, and she went up to get him. Suddenly, Bergen heard June gasp. “Come right away, there’s something wrong with my husband. I think he’s dead,” June said over the phone, which Bergen later recalled in the article. Before long, a police car and an ambulance arrived. “What is—what was the man’s name, Miss?” asked the young policeman, routinely filling out his forms. He showed no sign of recognition. Over the noisy growl of a tourist bus, June lamented her husband. “The poor thing,” she whispered as they carried Oscar out.

Sam Kashner is a Writer at Large for AIR MAIL. He is the co-author of several books, including A Talent for Genius: The Life and Times of Oscar Levant and Life Isn’t Everything: Mike Nichols, as Remembered by 150 of His Closest Friends