“I was saying to Patrick,” she said—as in Patrick McEnroe: the Davis Cup captain, brother of John, her husband and father of their three children—“that I have nothing to sell anymore, I’m just there. I’m so there. It’s just a sense that everything is O.K.”

Ms. Errico, 38, founded Bowery Babes in 2006, inspired by her prenatal yoga teacher, who stressed the importance of women banding together against the trials and isolation of impending urban motherhood. Now numbering more than 500, the Babes live in a loosely defined geographic bloc including the East Village, Soho, Chinatown and the Lower East Side (though residents of Williamsburg and the West Village have managed to sneak in, along with one stay-at-home dad). Their packed calendar includes weekly art classes, theater days, play groups, and postpartum “adjustment” parties at which wine is served and a counselor is present. (Alas, this reporter was not permitted to visit.)

Wearing a gray cashmere hoodie and a cherubic flush, Ms. Errico was clutching a BlackBerry, which buzzed incessantly. One mother was asking her to forward an email about a friend’s “strollercize” class to the group, which Ms. Errico hesitated to do because another Bowery Babe had her own stroller class. (She eventually relented since the classes were being offered in different neighborhoods.)

“Hey, Katia,” she said, answering the phone once before turning it off. “Is anything wrong? You need a nanny? Oh, how much is a nanny for a 24-hour stint? I can give you a couple of ideas. It’s basically like $150 a day. … I’ll call you back.”

Ms. Errico had less to say about her career—“I don’t really know what to say about it,” she said—than the Babes, of whom, she said, she has “completely the most tender thoughts I’ve ever had in my whole life.”

The first thing you see is a Ben Shahn–like collage of the face of Queen Victoria with a swastika in one earring and an eye and mustache that might very well belong to Adolf Hitler. The stage is instantly, startlingly set for the three hours of music and melodrama that follow. Arrogantly but amusingly based on John Gay's 18th-century The Beggar's Opera , Brecht and Weill radically compared the moral decay of Depression-ravaged pre-Nazi Berlin in 1928 with the sinister moral decadence of Victorian England in 1836, using the catwalks, bridges, pipes and ladders of the Industrial Revolution as a backdrop for a libretto with references to the St. James Club, Albemarle Street, the slums of Whitechapel and other London locations they knew only from books and maps. The result was a bawdy form of Zeitoper , a mixture of opera and music-hall entertainment for the masses created to reflect the spirit of the times-a style Weill followed throughout his career, even in his American works, with continued success. In 1928 The Threepenny Opera , known to the German masses as Die Dreigroschenoper , captivated everyone except the Nazis, who denounced the show as hysterical Communist propaganda, closed it down, and forced Weill and his wife, the legendary Lotte Lenya, to flee for their lives. But The Threepenny Opera would not die. Since the world thinks every new generation tops the list in the historic context of moral corruption, audiences always find fresh relevance in this creaky old war-horse. Countless revivals through the decades-including Marc Blitzstein's famous 1954 adaptation in Greenwich Village (the version that is appearing in Williamstown), in which Lotte Lenya reprised her original role of Pirate Jenny; a version in 1966 featuring Swedish marionettes; the well-received Lincoln Center revival with Raul Julia; and a catastrophic Broadway version in 1989 starring the pop star Sting-always manage to reinforce public fascination with The Threepenny Opera and meet with the same mixed reactions of analysis, skepticism and controversy as the first New York production in 1933, which closed immediately after the powerful drama critic John Mason Brown denounced it as "appallingly stupid".

Well, here it is again, through July 6-uneven and a bit of a jolt to the beatific summer repose of the Berkshires, but worth another look. While the band plays cabaret-style above the proscenium, the stage below surges with the impoverished underworld of the dying Weimar Republic, singing raucously about a British coronation that took place in a previous century with accents and costumes that clash comically from both time periods. When the show isn't overwhelmed by a teeming mob of blind beggars, hyperactive black nuns, undulating brothel floozies and Keystone Kops, all overacting madly without much cohesive or purposeful group movement, the action centers on Mr. and Mrs. Peachum (David Schramm and Randy Graff), venal exploiters of the miserable and oppressed who profit from their poverty, and their daughter Polly (beautiful, crystal-voiced Melissa Errico), who scandalizes them by marrying their archenemy Macheath, the lying, thieving, murdering leader of a gang of sewer rats who terrorize the slums. Macheath (immortalized by Louis Armstrong as "Mack the Knife") is faithful to nobody, and before the exhausting evening ends, he must deal with both the law and the women who crave and betray him-a whore named Jenny (Betty Buckley), the policeman's daughter Lucy Brown (Karen Ziemba), his own wife Polly, and the frustrated, neurotic Mrs. Peachum, who secretly wants him, too, but devotes her life to sending him to the gallows. The ladies are first-class. Betty Buckley has learned a lot about subtlety, reducing her usual shrieking to measured, beautifully articulated doses of sensuality on "Pirate Jenny." Karen Ziemba's "Barbara Song" is memorable. To assure a generous showcase for the talents of his diverse female stars, Mr. Hunt has even transposed Kurt Weill's haunting "Surabaya Johnny" from the score of Happy End for Ms. Errico to sing to Macheath's den of thieves. This great song is a staple in the repertoires of throaty nightclub singers everywhere, but in the context of The Threepenny Opera , it makes no sense at all. Why is the oversexed, newly married and deliriously happy Polly delivering a tragic, heartbreaking dirge in the underground hideout of a gang of thugs while dressed in an elegant white wedding gown?

Worse still, this production suffers from one fatal flaw-Jesse L. Martin, one of the original stars of Rent and a regular on Law & Order , in the pivotal role of Macheath. It's a piece of disastrous miscasting that deals the show a mortal blow from which it never really recovers. I admire the determination to be politically color blind (if not correct), but equal-opportunity casting does not always serve the best interests of the material creatively. As a stud who reduces all women to puddles of palpitating lust, Macheath must be big, dangerous, sexy and irresistible. Lacking energy and charisma, Mr. Martin seems no more viable as a denizen of the London underworld than Sammy Davis Jr. He probably cuts a fine figure in the right role, but without any sign of direction, he seems tentative, weak and frankly lost. No match for the women circling around him in showstopping turns who overpower him vocally and dwarf him physically, Mr. Martin just disappears. Woefully, he's less Mack the Knife and more Jelly's Last Jam.

More stylized German Impressionism in the concept would have made this a better (and more coherent) interpretation of the Brecht-Weill oeuvre . Still, there is much to admire, and when I glanced at my watch in the third act, I was surprised to realize I had been sitting for three hours already without boredom. One of the abiding truths in Williamstown is that there is no time to yawn. The Threepenny Opera will be followed by John Guare's Landscape of the Body with Lili Taylor, as well as new productions of plays by Dylan Thomas, Tom Stoppard and Henrik Ibsen, while the smaller Nikos stage will host the pre–New York tryout of a new play by A.R. Gurney; Nicholas Martin will direct Estelle Parsons in Alexandra Gersten-Vassilaros' Mother of Invention , starring Estelle Parsons, Bob Dishy and Matt McGrath; and the Nikos season will end in mid-August with a distinguished week-long cycle of all-repeat, all! -the great plays of Chekhov, with all-star casts yet to be announced. (Blythe Danner will be in one of them.) Are you getting the message? From the picture, is it clear why the Williamstown Theatre Festival is no longer just a summer happening for tourists, but a required destination circled on the maps of the cultured and wise.

Feel the Love

If you're stuck in the city, one of the most sophisticated and musically refined cabaret engagements of the year awaits you at the Algonquin's Oak Room, where the widely admired song stylist Sandy Stewart is appearing in an exclusive visit through Wednesday, July 9. Accompanying her unique interpretations of classic American songs with brainy and stylish arrangements that obviously reach from the heart is the sensational jazz pianist Bill Charlap. In case you no longer believe there is magic in the right gene pool, his father was the late Moose Charlap, the sensitive and talented Broadway composer whose shows included Mary Martin's Peter Pan . In case you are new to the music scene or just blossomed from the pistil and stamen of a Casablanca lily, Sandy Stewart is Bill Charlap's mother. Together, they make the kind of music you only hear about once every 10 years, if you're lucky. At the Algonquin, where they opened Monday, June 30, I know devoted diehards who plan to hear it for 10 nights in a row.

In the days when quality singing wasn't as rare as it is now, Sandy Stewart was a regular on television's long-running Perry Como Show and toured with Benny Goodman. Now that her sons Bill and Tom, both musicians, are grown men with careers of their own, she has resumed her singing with a wonderful family CD that features sons Bill and Tom on piano and bass and husband George Triffon on trumpet and flugelhorn. Bill Charlap grew up immersed in jazz and show tunes and toured after his second college year with Gerry Mulligan, Tony Bennett and others. Stardust , his recent CD of Hoagy Carmichael songs, is one of the most heavenly jazz collections I've heard in the past decade. Fast becoming New York's most critically acclaimed young pianist, he is already being touted as the one to take over where Bill Evans left off.

So why are they so special? Many of today's singers concentrate on technique. The results are often technically proficient yet emotionally chilly. Ms. Stewart never distances herself from the listener. She can sharpen the blurred lines between imagery and reality on a standard like "Ev'ry Time We Say Goodbye" and reveal hidden elements in Cole Porter's lyrics so boldly, bravely truthful they startle you into paying closer attention, even though you think you've heard the words before. Her certainty and confidence make fresh, pensive, underexposed ballads like Arthur Siegel's insightful "Where Is Me?" shine with the luster of impeccable phrasing, while Moose Charlap's devastating "I'll Never Go There Anymore" always leaves me emotionally shattered. But this lady can also swing. Her time shifts on jazz evergreens like "It All Depends on You" and "I Concentrate on You" rise like syncopated smoke rings nourished by neon. And she still sings "My Coloring Book," the hit song by Kander and Ebb which she introduced and kept on the Top 10 list for aeons, better than anyone else. Bill Charlap's clean lines and gorgeous chords rock his mom's voice as gently as cradles, and his improvisational riffs never fail to take my breath away. The fans who flock to Sandy Stewart's engagements on her increasingly rare trips to New York from her home in Florida are enthralled by her voice. They're here for the music, not the photo ops. Don't expect hair the color of raspberry Jell-O, throat tattoos, pierced tongues or freak contestants from reality shows buried under bling-bling in tacky Jimmy Choos. So drift into the Oak Room with ease. There is some love going on here, and it rubs off, in spades.

Fun in the Sun

For pure fun in the sun, Legally Blonde 2 is a cloudless way to spend 95 air-conditioned minutes with the delectable Reese Witherspoon. From the waif in movies by Robert Mulligan and Robert Benton to a power player worth $15 million a picture, she's surpassed the phonies to come a long way in a short time. For once, the overrated learns and talent earns. This time she's back as Elle Woods, the blue-eyed, twinkle-nosed Bel-Air bimbo turned Harvard Law School graduate, engaged to her dreamboat law professor (Luke Wilson) and invading Washington, D.C. All fired up after discovering that the birth mother of her miniature Chihuahua, Bruiser, is being held captive in an animal-research lab, Elle heads for Capitol Hill to pass a law against using animal testing for cosmetics. "I taught Bruiser how to shop online," she says. "I think I can handle Congress." Dressed in her best pink, two-piece Jackie O. knockoffs, she tackles D.C. the Elle Woods way, appealing to dog lovers and fellow sorority sisters, but gets out-maneuvered by a brittle, deal-making Massachusetts Congresswoman (Sally Field). Silly, harmless fun, with candy-floss style the color of Pepto-Bismol. Without the enormous skills of Reese Witherspoon, who also acts as executive producer, you could send this one straight to Blockbuster. With her, it is a blockbuster. The cast includes fine work by Bob Newhart, Dana Ivey, Regina King and Jennifer Coolidge, the direction by Charles Herman-Wurmfeld is tongue-in-cheek yet respectful of women, the script by Kate Kondell is hilarious without being idiotic. And there is an old-fashioned message. In the end, it's Elle who turns dirty politics upside-down in the style of Jimmy Stewart in Mr. Smith Goes to Washington , addresses both houses of Congress, and proves what a difference one inspired Barbie doll can make appealing to a woman's pocketbook in the land of the "free gift with purchase." Yes, there will be more: Elle's already got her eye on Hillary. At the end of Legally Blonde 2 , Elle's got her eye on the White House.

So far, he's not particularly well known and he doesn't have a girlfriend. But that doesn't mean he's given up. After all, this is New York, where everyone under 50 is secretly convinced that he or she is about to blow up huge any second now. And, at 33, Mr. Leaf has indeed written a play, about the Russian poet Aleksandr Pushkin, that was good enough to get James Wood, the hip literary critic of The New Republic , to have coffee with him. Mr. Leaf is also charming; he listens; he has good manners and the other nice-guy traits. He's tall, gawky, not bad-looking–perhaps catnip to a certain type of Ivy League woman.

But consider the downside. Mr. Leaf's posture is really bad. He slouches. He doesn't dress well, and the ladies don't like that. Worse, Mr. Leaf lacks the quality New York women adore: confidence. So far in 2000, Mr. Leaf has gained weight and has not had sexual intercourse.

He also lacks another quality women tend to find appealing: money. His father died in 1997, and the small inheritance he received is gone. Presently he has about $1,500 in the bank but owes $20,000 in student loans. He is being sued for $1 Million–a car accident in Morningside Heights.

But things may be looking up: The actress and singer Melissa Errico, who is married to sportscaster and tennis player Patrick McEnroe, met Mr. Leaf through a mutual friend from Yale University who used to sort of stalk her, and she has convinced the Irish Repertory Theater to give a reading of the Pushkin play in September. "He's a doll," said Ms. Errico. "I think he's going to be everyone's sweetheart, because of his personality. I am totally fascinated by him. I think he needs focus, professional focus."

Ms. Errico is Mr. Leaf's only brush with the shiny side of life. He has never been to the Hamptons. He takes dates to the Metropolitan Museum of Art and gets there early so he can purchase two passes for 50 cents. On the way home from a date, Mr. Leaf has the cab drop his date off, then, after taking the cab a more few blocks, he gets out and rides the subway. He gets his New York Times from recycling bins. Home is Flatbush, where he lives with his 88-year-old grandmother, Bessie.

"I lead a very dull life," Mr. Leaf will tell you. "I'm a 33-year-old man who lives in New York and I've never been unfaithful to a woman. I don't know how many people can say that. I think that's a small, small number. That's how dull my life is."

Early on a recent Sunday evening, Mr. Leaf was in his dining room, vigorously cutting cheese. He was wearing a blue sweater and jeans. He had $12 in his pocket.

"Do you like Cotswold?" he asked. Then he mentioned that he was quite certain that he was neurotic.

"Like the way I'm holding my arms right now," he said. "Very closed in. The body language is bad. I would say: very bad. I don't stand up straight. My appearance–I have all sorts of neuroses. My hair looks stupid, my nose is too large, my lips are too large–they go on and on. My voice is too nasal and a shade too high. My hands, the palms. You know, an aristocratic hand should have long, tapered fingers and a small palm. You see, I have this huge palm and these fat stubby fingers. They're grotesque."

He's also accident-prone. "I've broken my ankle, my wrist, my jaw, my nose, several of my fingers," he said. "I've separated my shoulder. I've injured my knee twice. Two kidney operations."

Mr. Leaf grew up in Trenton, N.J., the son of psychologists. "I was the third child in three years," he said. "So I think I was actually a surprise to them. Let's hope it was a happy surprise."

At 6, Mr. Leaf scored 211 on an I.Q. test. He attended the exclusive Princeton Day School. "All the kids had lots of money and I was this very neurotic Jewish kid who did not fit in," he said. "I used to read Shakespeare on the school bus. I wouldn't say I had zero social awareness because that's giving me too much credit. I would say less, markedly less."

Mr. Leaf was cast as the villain in a school musical; his voice was so bad he was ordered to speak his lines. He read a lot and ended up at Yale University, where he drank more than he studied. After college, he worked as a security guard, a shoe salesman, a receptionist, a messenger, a news clipper and a substitute teacher.

After trying to make it as a game show champion in Los Angeles, Mr. Leaf took a year off to listen to Beethoven, read and write sonnets. He wrote a play. "I read it and said, 'You know, this is a lot better than most of what's being staged.' On the basis of that I started to think maybe I should be a writer." So far he's written nine plays, none of which have been performed, and a comic novel, still unpublished, about the 1960's radicals who made up the Students for a Democratic Society.

In between bites of cheese, he said women had been "a source of great pain."

"I was passionately interested in a woman who was bisexual, and she suggested we get together," he said. "I'd been interested in this woman for about 10 years, literally. We got together and I proceeded to get drunk on the date and made some comments that she might have misconstrued as being homophobic. She immediately bridled. And I thought to myself, 'Ten years! What am I thinking ?'"

He told a story about another date: "So we go to this falafel place, she's wearing this long sweater, and I said, 'Why don't you take this sweater off?' And she said, 'I can't do that because I just slit my wrists and I don't want people to see the scars.' Then she rolled up the sleeves a little bit so I could see the scars. Then the waiter comes over. I ordered and said, 'What would you like?' And she said, 'I can't eat anything because I'm bulimic and I'm just going to throw it up anyway.' And then she took her hand and she started stuffing it down her throat, with the waiter there, to demonstrate. Then I said, 'What would you like to do with the rest of the evening?' She said, 'Well, since I'm an alcoholic, I'd like to go out drinking.' This is a true story. This was a Yale student, by the way. They're getting the best and the brightest, you know. I would say that was certainly an unfortunate evening."

His grandmother Bessie sat down.

"He has a sweet temperament," she said. "He's very good for conversation. Very easygoing. We don't get in each other's way. He takes care of himself so beautifully. He does his own food, unless I make something that I know he likes, and then he will join me.

"He's very knowledgeable," she continued. "If I'm stuck and the ladies are coming over and the floor is dusty, he'll vacuum on his own. Very aware! He has a friend in California and we chat, and he thinks Jonathan's a genius: 'He has to be heard from!'"

Did she agree? "I don't know," she said. "I know a lot of people who are very bright."

I asked Bessie if her grandson brought dates to the house.

"No, nobody," she said. "You're our first guest, as a couple." Then she brought out some macaroons.

A few days later I called Ms. Errico, the actress, to ask her about Mr. Leaf. Ms. Errico has starred in Broadway shows such as My Fair Lady and High Society , and she has a part in the current movie, Frequency .

She said that in addition to encouraging the Irish Repertory Theater to do a reading of Mr. Leaf's play, she was interested in developing and starring in a romantic-comedy screenplay he had written. She said he comes to hear her sing, and then leaves long messages on her answering machine about how much he loved the performance. She said she found him endearing.

"He unravels right in front of you," she said. "He gets these flashes of brilliance, he's really assertive, and then he just unravels. He's like a mad scientist. He never quite eats when I see him, it's almost like he's too focused to eat, because he's waiting to meet me. But you see, I understand people like that, I'm forgiving of that. I'm not like, 'Oh, no, he's not a hot Manhattan File guy.' That's cool by me. In fact, that's probably why I talk to him more than I talk to people who are smooth. He's not smooth, you know."

Early one morning a few weeks later Mr. Leaf called me.

"Hey, you ever go pick up babes at Bryant Park Grill?" he asked. We agreed to meet there the next night.

He showed up wearing a white button-down shirt, gray pleated slacks and brown comfortable shoes. He'd taken a job as a copy editor for an online brokerage, with offices in Jersey City, N.J. But the big news was that he had traveled to Washington, D.C., to meet with The New Republic' s James Wood. Mr. Leaf had sent the Pushkin play to an editor at The New Republic , who passed it on to Mr. Wood. The two men ended up in a coffee shop. Mr. Wood said he found Mr. Leaf to be "a slightly romantic figure, because he has this sort of slouching, rather intense, sort of a hero-from-Dostoevsky kind of manner." He also liked the play. "He's pulled off the rare achievement, in the modern age, of writing convincing verse drama which is also good dramatic speech," said Mr. Wood.

At the Bryant Park Grill, Mr. Leaf said there weren't too many people like himself, attempting verse drama. "I mean, I've read Dryden's verse plays, I've read Shelley's verse plays, I've read Browning's, I've read Tennyson's, I've read Eliot's, Byron's–they're almost all terrible."

Around us, the after-work singles were checking each other out as techno music played in the background. Mr. Leaf was ready to prowl. He explained his strategy: approach a woman he is attracted to, and claim that his "friend" thought she was incredibly beautiful and wanted to meet her. He wasted no time chatting up three women. I asked them for their impression of him.

Paula Karstens, a 32-year-old director of a technology stocks division at CIBC Oppenheimer, said, "I see a lot of violet in his aura."

She was wearing a revealing pink silk shirt, a pair of tight silk pants that she said she bought in Rome, and high heels.

"You know, Paula," Mr. Leaf said. "I don't know if I'm going too far afield, I don't know if I'm advancing a view that's questionable or dubious in nature, but I think you have some instinct towards mocking."

Mr. Leaf spotted someone else and walked in her direction, saying, "This woman is stunning."

I showed Ms. Karstens a copy of Mr. Leaf's play. "So is he really brilliant?" she said. "Because I love brilliant men. I need a new boyfriend. Is he gay? Does he have a girlfriend?"

She called her girlfriends over. "I'm reading a play by my new boyfriend!" she said. "I like his name. Did he change it to become a playwright?"

Mr. Leaf returned, carrying two whiskey sours.

"Jonathan, I read this play, I think it's brilliant," Ms. Karstens said. "I have one question, though. Do you think it might go over people's heads?"

Mr. Leaf gave her a look and walked off, apparently to deliver the whiskey sours. He was soon in conversation with a 23-year-old blue-eyed brunette named Elizabeth Drennen, who was with two girlfriends. Mr. Leaf did his spiel–his friend thought she was beautiful–and was invited to sit down. He focused on Ms. Drennen. She said she was from Birmingham, Ala., that she used to be a Sunday school teacher and was now a publicist at Time Warner Books. She asked Mr. Leaf for his age.

"Oh, my boyfriend's 34," she said. "He's great and really wonderful." She added that they were taking a month-long break.

"I, unlike the rest of these people, am not of Christian faith," Mr. Leaf said.

"O.K., you're what, Jewish?" Ms. Drennan said. "That's O.K., Kevin's half-Jewish."

Mr. Leaf told her she was beautiful but would look better with glasses. "Do you wear glasses?" he said. "You know, there's a positive correlation between nearsightedness and I.Q. I have perfect vision."

Mr. Leaf got up, and the women discussed him.

"I like him," Ms. Drennan said. "He's adoring. He's insightful. He's definitely not a Shylock, with his comments. He's definitely tricky. Totally a line-er. A tricker. But I tell you what I like, and this is me, and I'm sure all women are like this, but he gives a lot of attention. Men who give you attention–love it, you just love it. Where is he?"

Mr. Leaf had gone back to Ms. Karsten. She was imitating a geisha.

"My name is Shi Ho," Ms. Karsten said. "I'm from Kyoto, Japan. I'm a geisha. We really, really like to give a man pleasure! We pour the sake, hee! Hee-hee-hee! And then we give massage ."

Mr. Leaf disapproved. "Remember that guy who got fired from Morgan Stanley for those nude pictures?" he said. "You keep talking, that's what's going to happen."

"You're fascinated by me," she said.

Mr. Leaf confessed that he was.

Ms. Karstens began dancing a jig, stomping loudly. Then she backed up against Mr. Leaf and rubbed herself against him. Head on his chest, she looked up and asked him for a light. Steadily, Mr. Leaf lit her cigarette.

"You know what's amazing?" he told her. "It's how sexually confident your body language is and how neurotic mine is."

Meanwhile, Ms. Drennen and her friends were still talking about Mr. Leaf.

"Why does he slouch?" Ms. Drennen said. "He shouldn't slouch. If he sat up straight and acted like he was, like, more of a man , people would sort of gravitate towards him more. Act like somebody and you will be somebody. I love confidence. Dishonest or not, if you pretend to be something, eventually you will become something."

Later that night, Mr. Leaf went home to Flatbush alone.

The move to 55 Central Park West, an Art Deco building near West 66th Street, should be a big relief to the fashion designer, who in the last year has gained something of a reputation for capriciousness in the high-end real estate market. Though Ms. Karan and her husband, sculptor Stephan Weiss, spent two years happily ensconced in a rental at the San Remo, a co-op at 145 Central Park West near West 74th Street, her desire to buy a home took on newfound urgency on June 30, when their lease expired.

Ms. Karan faced some heartbreak when she was asked to leave Central Park West, considering the lengths to which she had gone to make the rental apartment photogenic enough for glossy magazines. But according to comments by Ms. Karan in The New York Times –which published some shots of the place, post-mortem, on Oct. 24–every last detail was transportable, further illustrating her homeless status. From the San Remo, she moved into a 5,000-square-foot loft on Wooster Street, where she's been cooling her heels.

"She's been looking for four years, since before she moved into the San Remo," said one of the half-dozen brokers with whom Ms. Karan has worked this year.

"Someone said to me she'd been looking for 15 years," quipped another broker who also devoted time to the designer's search.

After a couple of disappointments–the San Remo lease, which expired when the owner balked at Ms. Karan's desire to buy; a turn-down by the prestigious co-op at 10 Gracie Square, where she was in contract for a 15-room apartment costing $5 million–the designer seemed poised to buy a condominium at the Alfred, a high-rise building at 161 West 61st Street, last July. But Ms. Karan never signed the contract for just over $5 million on the property. By the end of the summer, she was back on the market, represented by a broker from Edward Lee Cave Inc.

Around Labor Day, Ms. Karan and Mr. Weiss looked at the 16th-floor apartment of Seymour Stein, the chief executive of Sire Records Group and an on-and-off resident of the building for about 10 years. The apartment, a full-floor swath being marketed by broker Linda Stein, Mr. Stein's ex-wife, for $11 million, is 6,000 square feet and has incredible views of Central Park. However, the property needs a good deal of work: Mr. Stein bought two neighboring apartments in succession with the intention of combining them, but never really got around to it. "There's a hole in the wall so you can walk through," explained a source familiar with the space, underscoring the fact that it needs some imagination.

Considering the building's history, the co-op board could hardly turn Ms. Karan and her husband down based on their celebrity status. Over the years, 55 Central Park West has been home to designer Calvin Klein, who sold his penthouse apartment to Steve Gottlieb, the president of TVT Records, for $8.6 million in February; media mogul Jann Wenner and his boyfriend Matt Nye, who rented another, four-bedroom apartment owned by Mr. Stein several years ago; and ABC News correspondent Forrest Sawyer, who bought the Wenner-Nye apartment in 1996, after the couple moved out, for $3.2 million. (Mr. Sawyer sold his property late last year.) Restaurant reviewers Nina and Tim Zagat also live there.

Still, the co-op's board members became infamous for splitting legal hairs earlier this year, when they twice rejected power couple Diane Sawyer, currently the co-anchor of ABC's Good Morning America , and her filmmaker husband Mike Nichols on their contract to buy what is now Mr. Gottlieb's penthouse.

"Look, if she's got the money and the assets and all that, I don't see any reason that she shouldn't have the apartment," said a broker familiar with Ms. Karan's plans. "And she's looked long enough that she's identified what she wants, and I think that's a good one for her. And it'll get two people who took a long, long time to make up their minds resettled … every broker who knows of them will get a chuckle."

Ms. Karan's publicist declined to comment.

SOHO

PAT McENROE CARRIES MELISSA ERRICO OVER THRESHOLD AT 285 LAFAYETTE STREET. Doubles tennis player Patrick McEnroe and his new bride, actress Melissa Errico, purchased a two-bedroom apartment at 285 Lafayette Street for $1.53 million in August. The couple now shares an address with rock star David Bowie and supermodel Iman.

Mr. McEnroe is the 33-year-old kid brother and sometime doubles partner of tennis pro John McEnroe. He owns an apartment at the Eldorado, a co-op at 300 Central Park West near 90th Street, where his brother's ex-wife, the actress Tatum O'Neal, lives along with other celebrities like Alec Baldwin and Kim Basinger. Now a tennis commentator for ESPN and CBS Sports, Mr. McEnroe recently married Ms. Errico, a Broadway actress who had a role on the failed TV series Central Park West in 1995.

The couple's Lafayette Street apartment is one of a group of newly renovated properties atop a classic artist-in-residence loft building between Prince and Houston streets. Their 2,660-square-foot space, which carried an asking price of $1.5 million, is similar in character to that of Mr. Bowie, who bought two contiguous apartment units: All the new condos have Rutt custom cabinets, polished nickel vanities, Brazilian hardwood floors and restored turn-of-the-century details. During the construction process, which was completed in the middle of the summer, the couple was allowed to tweak the décor, such as choosing the finish on the floors, which they darkened, and opening up the kitchen walls a bit.

"The apartment has a lot of charm and has an old yellow pinewood beam running through the ceiling, which has been stripped and left exposed," said a source familiar with the property. "It's very quiet, and has a view of the Old St. Patrick's Cathedral," on Prince and Mott streets.

UPPER EAST SIDE

4 East 62nd Street (Curzon House)

Two-bed, 2.5-bath, 1,400-square-foot prewar condo.

Charges: $1,500. Taxes: $1,600.

Asking: $1.595 million. Selling: $1.5 million.

Time on the market: six months.

BORN TO RENT, THEN SELL. Talk about a rebound! Ten years ago, when she was divorced from rocker Bruce Springsteen, actress Julianne Phillips bought this condominium off Fifth Avenue for a mere $300,000. Right around that time, the building's management refurbished all the apartments, and Ms. Phillips wound up with a swank property that she began to rent out, most recently to an executive at a major investment bank for $13,000 a month. But when Ms. Phillips elected to sell the condo, it became a little less fabulous: the tenant was always in residence–in the course of six months, only three potential buyers actually passed through. The good news was that two of the three shoppers were interested. In the end, the apartment went to a couple in their 50's who were moving across town from their town house off Central Park West. They have a dog, they didn't want to give up the park. Plus, Joan Rivers lives right across the street. Broker: Sotheby's International Realty (Dolly Lenz).

455 East 86th Street (Channel Club)

Two-bed, two-bath, 1,325-square-foot condo.

Asking: $650,000. Selling: $650,000.

Charges: $765. Taxes: $1,016.

Time on the market: three days.

APARTMENT SWAP, MINUS THE LITTLE GIRL. The sellers lived in this 25th-floor apartment for about five years, but apparently East River views, a south-facing balcony, washer and dryer, customized closets and a fully equipped kitchen (with microwave and dishwasher) just weren't enough. So the couple (he's a managing director at Brean Murray & Company, the investment banking firm; she works for Forbes magazine) and their daughter are moving on. Their apartment sold in just three days at full asking price. The buyers are an American attorney and his French graduate-student wife. His stepmother, a broker, tipped them off to the sale, and they made an offer immediately upon seeing the apartment. The former owners will be moving into a spacious apartment, also in the Channel Club, which went up in 1987 and has a doorman, concierge, indoor pool and gym. Très bien! Broker: Douglas Elliman (Branko Vujanic).

CHELSEA

210 West 21st Street

Two-bed, one-bath, 900-square-foot prewar co-op.

Asking: $300,000. Selling: $300,000.

Charges: $802; 60 percent tax-deductible.

Time on the market: one day.

TELEGRAM MAN ANNOUNCES NEW ADDRESS. A sales representative with Western Union paid $175,000 for a one-bedroom apartment on the fifth floor of 233 West 21st Street, a cozy block between Seventh and Eighth avenues. After a paint job and a few improvements to the bathroom, the apartment was nice enough, but at 600 square feet, it was still a little bit cramped. Moreover, the owner had fallen in love with a Columbia graduate student, and the couple wanted a place to share. The sales rep called broker Mark Midensky, who had found him the one-bedroom apartment, for advice. Lucky for him, Mr. Midensky was in the process of trying to sell an apartment just across the street with two bedrooms, an office and an open living-dining area. Before long, the couple had crossed the street, and a Wall Streeter, fresh out of business school, had taken the smaller apartment off their hands. Broker: William B. May Company (Mark Midensky).

TRIBECA

10 Jay Street

Two-bed, two-bath, 1,350-square-foot co-op.

Asking: $535,000. Selling: $490,000.

Charges: $1,001; 45 percent tax-deductible.

Time on the market: six months.

TAKE TWO ON THE COBBLESTONES. A cinematographer and his producer girlfriend were living in the Village and wanted to stay there, but couldn't find anything acceptable within their price range. After some disappointing excursions, their broker, Linda Partland, took them to TriBeCa, where she told them they would be able to afford more space. Whatever! But Ms. Partland's hunch proved to be accurate: The couple was instantly enamored of this building, recently converted to a co-op, on Jay Street, a cobblestone block between Greenwich and Hudson streets. The sellers were a family of four who, after 10 blissful years of downtown living, were relocating to Australia; their imminent move, combined with the apartment's need for a facelift, allowed the buyers to shave $45,000 off the asking price. To create a more loftlike space, they intend to take down some walls and expose the apartment's inner columns–which should allow a little more light to filter in, even in the back of the building. Broker: Corcoran Group (Linda Partland and Perrie Gurfein); Douglas Elliman (Mike Chapman).

WATER MILL, L.I.

Fordune Drive

Two-story house.

Asking: $2.35 million. Selling: $2.385 million.

Time on the market: four months.

HOTEL HEIR GIVES HIS FAMILY HAMPTONS ROOM ASSIGNMENTS. After a year and a half of searching for just the right Southampton, L.I., fix-me-up, real estate executive Rick Hilton, his wife, Kathy Hilton and their four children settled on this two-story property in the estate section of Water Mill, right on the border of Southampton Village. The 10-year-old house, which was half-built when the seller purchased it (he oversaw the rest of the construction process, customizing along the way), has seven bedrooms and seven and a half baths, so everyone gets his or her own room. There's also a swimming pool, a three-car garage and hedges surrounding the 2.7-acre property for privacy's sake. Still, the place needs renovations, so the idea is to get it ready for weekend use by next summer. The family maintains residences in Manhattan and in Los Angeles, where Mr. Hilton (the son of Barron Hilton, chairman of the eponymous hotel-management conglomerate) runs a real estate firm entitled Hilton & Hyland. This past summer, while they were waiting for the contract on their Water Mill house to close, they had to rough it by touring through Europe. Broker: Allan M. Schneider Associates (Sandi Pullman); Mrs. Condie Lamb Agency (Kim Hovey).

Broadway pros does it take to cause a complete power failure? Answer: all of the misguided people it took to put together High Society . This numbing musical is so bad, it makes you consider taking back some of the things you said about The Capeman .

Just about everything goes wrong in this ill-advised attempt to turn Philip Barry's The Philadelphia Story into a musical croquet match. When M-G-M tried it back in 1956, moving the action from Philadelphia's Main Line to Newport, R.I., with a sparkling score by Cole Porter, they mined box-office gold. It was a great idea because the setting included the Newport Jazz Festival, providing Bing Crosby, Frank Sinatra and Louis Armstrong with an opportunity to blast off musically. The ragtag Broadway version that just opened at the St. James Theater not only dumps one of the score's most swinging tunes, "Now You Has Jazz," but digs up superfluous Porter tunes from other shows for padding.

Transferring the action to Oyster Bay, L.I., in 1938, for reasons nobody can decipher, is bad enough. Nobody does anything in Oyster Bay but guzzle martinis until they're stinking drunk. Just about everybody on stage in High Society falls over the lawn furniture in various states of inebriation while massacring Cole Porter, but worse than that, they are barbecuing the wrong lyrics. Any time a creative team behind a Cole Porter show figures they've got to rewrite and therefore improve Cole Porter, then, folks, we've got trouble in River City.

As Tracy Samantha Lord, a glacial beauty who lacks "an understanding heart," Katharine Hepburn made it difficult for future generations of lithe and languorous actresses to attempt the role she made famous (although I admit Dorothy McGuire once triumphed and even topped her). At M-G-M, Grace Kelly tackled the musical version with a range of about eight notes, so the current collaborators understandably had to alter just about everything to provide a repertoire suitable for the accomplished Melissa Errico, including a few numbers made famous by Ethel Merman and others.

This is a good thing, because Ms. Errico can sing out, Louise. This is also a bad thing, because songs like "Ridin' High," "Let's Misbehave" and "It's All Right With Me" are not only irrelevant and better suited to a cabaret act, but intrude rudely on the proceedings and do nothing to move the plot along. Everything, from the tin-can arrangements by William David Brohn to the additional lyrics by Susan Birkenhead, seems to be in slow motion. Everything is sung at the wrong tempo; a song like "Who Wants to Be a Millionaire," sung so charmingly by Mr. Sinatra and Celeste Holm in the movie High Society , cries out for pace. Even polished pros like Randy Graff and Stephen Bogardus find themselves swimming through sludge like crustaceans crawling their way out of a gumbo pot.

Toiling laboriously to overcome it is the cast, including Mr. Bogardus as Mike, the reporter covering Tracy's wedding; Marc Kudisch as George, the stuffed-shirt fiancé everyone hates; and sun-kissed Daniel McDonald as Dexter, the dapper, mischievous ex-husband, fresh from Steel Pier and none the worse for wear. They're fine as can be in a production that confines them to dinner jackets that serve more like straitjackets, but only John McMartin as the tipsy, addled, girl-chasing Uncle Willie brings any fresh character ideas to the limp proceedings.

Much has been made of Anna Kendrick as Tracy's kid sister Dinah. She's a Little Iodine who mugs annoyingly and belts like Merman in Mary Jane shoes, but when a child the size of a marzipan pineapple steals an entire Broadway show, you know there's disaster in every other corner of the stage. What kind of desperate, delusional director would ask a road company Annie to sing "I Love Paris" from Can-Can ? I saw it. I heard it. I still don't believe it.

As the centerpiece of this highfalutin fiasco, Melissa Errico is a Technicolor dream, but the magic she brought to the Encores! production of One Touch of Venus is, through no fault of hers, never duplicated. You have to work hard (or hardly work) to make Ms. Errico look flat-chested, but her 30's gowns work as cruel sabotage, while Ms. Graff, as the cynical Eve Arden clone from a scandal magazine, wears nothing but ugly stripes that make her look like a moving cafe awning. Meanwhile, the boring gaps between boring scenes are bridged by an eight-member household staff that seems to have wandered in from a musical version of Upstairs, Downstairs . They've all been directed (clumsily, if you ask me, by Christopher Renshaw) to milk every attitude for maximum phoniness. Despite the magnums of champagne consumed on stage, the fizz is missing.

The sets, the skies, the Long Island sunsets, the furniture, even the proscenium arches all look like melted sorbets. (The predominant color is seasick green.) I've never seen so many nauseating plastic cabbage roses. They've taken the ginger out of Philip Barry and decimated all memories of the snap in the M-G-M musical. Were Barry alive today to see what they've done to his High Society , he'd probably make a citizen's arrest. This may be the best senior-class musical ever produced in South Bend, Ind. It is not, by any stretch, good enough for the standards we've come to expect from Broadway.

Pity Downey's Two Hip Chicks

Robert Downey Jr. is out of jail and on his way to being clean and sober. (One hopes, in the process, he rediscovers the talent that earned him justifiable praise for Chaplin .) Unfortunately, his first movie since he kicked all those well-publicized drugs could send him back to rehab out of sheer depression. It's called Two Girls and a Guy and, in my opinion, it's unactable, unthinkable and unreleasable. I don't know what kind of shape the actor was in when he made it, but he looks like he's hanging from a light fixture. If you're one of the unfortunate victims who actually sits through it, you may just want to hang yourself.

In this piece of pretentious trash, two hip chicks are waiting on the doorstep of a New York loft for their boyfriends to come in from the airport. When they discover they are waiting for the same guy, they don't just hail a taxi and write him off as a lost cause. They break into his apartment and wait for sweet revenge on the lying, cheating, manipulating, two-timing jerk who has betrayed them both. Heather Graham and Natasha Gregson Wagner are beautiful and feisty. Mr. Downey is the conniving pathological liar they love. And they spend the next hour and a half talking themselves to death in a film that was shot in 11 days and looks it.

Hamming it up outrageously in the worst performance on the screen this year, Mr. Downey is so obnoxiously self-indulgent it's a total mystery why either of these foxy babes saw anything in him in the first place. How many people in your experience do you know who come home after a long plane trip and sing the entire song "You Don't Know Me"? Don't you check the fridge to see if the milk is bad? Don't you rifle through the mail or check the answering machine? This egomaniac bellows and croons off-key. He lounges naked in the bathtub. He phones his neurotic mother every 10 minutes. He crawls around on the floor in his underwear, puffy, overweight and unshaven, covered with pimples. In the rare instances when he runs out of business, he even smears himself with chocolate syrup. It's a performance I can only describe as repulsive.

The girls call him "creep" and "scumbag," and that's just the nice part. Still, they beg him for sex. They even make a stab at a three-way. (Ms. Wagner's character confesses she's a part-time lesbian anyway, but Ms. Graham's character passes.) Everyone mewls and whines and screams. When attention lags, they throw things. That passes for acting. And it's all been directed and written (as if one sin were not enough) by James Toback, whose lack of talent is surpassed only by his megalomania. As a writer, his dialogue is nothing more than numbing amateur psychobabble. As a director, he allows the actors to throw themselves all over the place in one claustrophobic room with a minimum of blocking and a maximum of confusion.

Nothing in Two Girls and a Guy is believable or real or natural. It's a pointless waste of time, and all I could think of was what Ms. Wagner's mother–the late, great Natalie Wood–would make of all this.