25 Classic Hillary Clinton (Getty Images)

The Odd Couple ’08

By Ben Smith

[Ed. note: This article was originally published on June 20, 2005.]

Hillary Clinton hasn’t had her Hayman Island moment. Yet.

Hayman is a resort off Queensland, Australia, to which Rupert Murdoch flew Tony Blair in 1995 for the annual conference of his right-of-center media megalith, News Corp.

It was a crucial step in the complex and surprising negotiation between the two men that would boost Labour’s Mr. Blair up the little stoop and through the door at 10 Downing Street two years later. Read More

25 Classic Anthony Weiner (Getty Images)

Anthony Weiner, In Mayoral Run, Models On Koch

By Phoebe Eaton

[Ed. note: This article was originally published on March 7, 2005.]

“If I see Anthony Weiner, I’m gonna kick him in the balls!”

Woody Johnson was kidding around at the annual winter cocktail party for the Queens County Democrats that was underway at Antun’s, a lively wedding-reception rathskeller in Queens Village. The owner of the Jets had been making the rounds, cranking up support for a stadium on the site of the M.T.A.’s West Side railyards that would double as a stage for the 2012 Olympics. Only suddenly, he had a gate-crasher: Days earlier, Madison Square Garden’s territorial operator Cablevision offered $600 million to the M.T.A. to plunk some apartments and offices on the site-six times more than what Mr. Johnson was bidding. This was just the beginning: TransGas would soon be flashing $700 million at the M.T.A., and the state of New Jersey was jumping up and down to sell the Jets on a less magnificent setup entirely. It was turning into a messy food fight, and everyone knew it. Read More

25 Classic sex and the city

Loving Mr. Big

By Candace Bushnell

[Ed. note: This column was originally published on April 24, 1995.]

A 40-ish movie producer I’ll call “Samantha Jones” walked into Bowery Bar and, as usual, we all looked up to see whom she was with. Samantha was always with at least four men, and the game was to pick out which one was her lover. Read More

25 Classic John Updike

Twilight of the Great Literary Beasts: John Updike, Champion Literary Phallocrat, Drops One; Is This Finally the End for the Magnificent Narcissist?

By David Foster Wallace

[Ed. note: This article was originally published on October 13, 1997.]

“Of nothing but me … I sing, lacking another song.”

-John Updike, “Midpoint,” 1969

Mailer, Updike, Roth-the Great Male Narcissists who’ve dominated postwar realist fiction are now in their senescence, and it must seem to them no coincidence that the prospect of their own deaths appears backlit by the approaching millennium and on-line predictions of the death of the novel as we know it. Read More

25 Classic Woody Allen (Getty Images)

The Dark Bourgeois Heart of Woody Allen

By Philip Weiss

[Ed. note: This article was originally published on May 25, 1998.]

Woody Allen often likens his work to magic, and his haunts in the Manhattan Film Center inside the Beekman apartments feel a little like the magician’s back rooms. They are not Upper East Side interiors one would ever see in his movies, they’re scrunched and the slightest bit shabby, with a sense of underpaid help flying around with the fax machine shoved under the coat rack. On Dec. 2, the day after Mr. Allen’s 62nd birthday, I was shown into a screening room that was also doing double-duty, with record albums on one wall and canisters of film along the other. Read More

25 Classic John F. Kennedy, Jr. (Getty Images)

John Kennedy, New Yorker

By Frank DiGiacomo

[Ed. note: This article was originally published on July 26, 1999.]

New York doesn’t have room to bury its very important dead. Ulysses Grant, of course, is up on Morningside Heights. A few old bishops rest in the crypts at St. John the Divine, and some cardinals lie under St. Patrick’s. Some dusty patriots fill the yard way down beside Trinity Church. But when Gershwin or Jacqueline Kennedy Onassis or even Thurman Munson dies, they’re honored here, then sent away for burial in greener, more sacred ground, and New York feels palpably lonely without them. Read More

25 Classic Woody Allen watches a Knicks game (Getty Images)

Notes of a Know-Nothing Knicks Fan

By Woody Allen

[Ed. note: This article was originally published on May 25, 1998.]

I am always asked to write about basketball. People labor under the mistaken impression that, since I attend the Knicks games and have done so regularly for over 25 years, I’ve learned something or that I have insights and observations that are worth listening to, but they are wrong. Read More

25 Classic The New York Times (Getty Images)

The Kingdom and the Tower

By Gay Talese

[Ed. note: This article was originally published on June 26, 2007.]

When Arthur Gelb joined The New York Times as a copyboy in 1944, the uniformed elevator men wore white gloves, the desk editors donned green eye shades, and reporters making phone calls from the third-floor newsroom had to be connected by one of the dozen female operators seated at the 11th-floor switchboard (perhaps the most vibrant center of gossip in all of New York); and up on the 14th floor, adjoining the publisher’s office, was a private apartment visited on occasion by the publisher’s mistress—and there was also nearby a bedroom for the publisher’s valet, a gentleman of high moral character and undaunted discretion. Read More

25 Classic At left, Nick Denton, with The Guardian editor-in-chief Janine Gibson (Getty Images)

The Gawker King

By Tom Scocca

[Ed. note: This article was originally published on October 3, 2005.]

On Sept. 21, Arianna Huffington, the Los Angeles social catalyst, former California gubernatorial candidate and self-appointed anti-Drudge of Web hostesses, tore off her shoes, jumped up on Nick Denton’s coffee table and anointed him: Mr. Denton, said the Amazonian queen of L.A. society—a world that one of Mr. Denton’s 14 Web sites assesses and reports on—is “the Rupert Murdoch of the blogosphere.” Read More

25 Classic Jayson Blair (Getty Images)

‘So Jayson Blair Could Live, The Journalist Had to Die’

By Sridhar Pappu

[Ed. note: This article was originally published on May 26, 2003.]

“That was my favorite,” Jayson Blair said. It was the morning of Monday, May 19, and the disgraced former New York Times reporter was curled in a butterfly chair in his sparsely furnished Brooklyn apartment. He was eating a bagel and talking about one of his many fabricated stories—his March 27 account, datelined Palestine, W.Va., of Pvt. Jessica Lynch’s family’s reaction to their daughter’s liberation in Iraq. Read More

25 Classic Kari Ferrell (Getty Images)

The Hipster Grifter

By Doree Shafrir

[Ed. note: This article was originally published on April 15, 2009.]

It’s likely that when Kari Ferrell walked into the Vice magazine offices in Williamsburg, Brooklyn, last month to interview for an administrative assistant job, they thought they’d hit the jackpot. Ms. Ferrell—petite, 22 years old, of Korean heritage—had a huge tattoo of a phoenix across her chest and a cute pixie haircut. She was talkative, funny, charming, adorable. She had a tattoo on her back that read “I Love Beards.” She told them she’d been working for the New York office of the concert promotion company GoldenVoice, which puts on huge rock festivals like Coachella near Palm Springs, Calif., and that she’d moved to New York from Utah just a few months earlier. They hired her on the spot. Read More

25 Classic Illustration by Thomas Pitilli.

The Luxury Rental Girlfriend

By Lisa Taddeo

[Ed. note: This article was originally published on January 22, 2013.]

Jack is in his 30s. He’s good-looking, makes money and has a nice apartment, and in this city, what all that gets you is almost everything. He meets me on Greenwich Street one morning for black coffee. Two girls he knows come walking by. He smiles, and his blue eyes are warm, but on one girl’s face you can see that whole wringing week she waited for a call. Read More

25 Classic Michael Musto (Getty Images)

Meet the Columnists Who Dish It Out

By George Gurley

[Ed. note: This article was originally published on April 17, 2006.]

That’s Funny, Kids. That’s Funny

A typical Cindy Adams item: Photographer Peter Beard goes into the bush, gets stomped by an elephant and his pelvis shatters in 22 places. Six months after he heals, he goes back, and another elephant charges him. Director Renny Harlin is making a documentary about Mr. Beard. What’s Cindy’s last line? “This guy doesn’t need a director, he needs a new travel agent.” That’s funny, kids. That’s funny. Read More

25 Classic Peter Braunstein

Peter Braunstein, WWD Writer Turned Tabloid Monster, Still Has Issues

By Aaron Gell

[Ed. note: This article was originally published on December 13, 2011.]

Editor’s Note: This story is excerpted from Aaron Gell’s Kindle Single, Speak of the Devil, available at Amazon.com for Kindle and iPad, and at barnesandnoble.com for Nook.

One day in October 2010, Peter Braunstein’s monthly subscription copy of W magazine arrived right on time. It was one of the first under the direction of a new editor, Stefano Tonchi, and the cover featured Ryan Gosling and Michelle Williams in an artfully staged embrace: a red-lipsticked Ms. Williams, staring out at the viewer as if surprised by the camera; Mr. Gosling cradling her head with the tenderness of a ballet dancer. Read More

25 Classic The cast of "Seinfeld" (Getty Images)

The Final Seinfeld: I Told You So!

By Ron Rosenbaum

[Ed. note: This article was originally published on August 21, 2006.]

I’m sorry, I just can’t resist. Vindication this sweet, this complete, is just so rare and beautiful, I’m going to have to savor it at length. I’m going to postpone the second part of my exploration of David Berlinski’s heretical vision of the origins of man and the universe I promised in last week’s column to take one final, absolutely irresistible I-told-you-so shot at Seinfeld. Read More

25 Classic Barbra Streisand (Getty Images)

Barbra’s Farewell–A City Verklempt

By David Rakoff

[Ed. note: This article was originally published on October 2, 2000.]

It is High Holy Days weather in New York. And if you were to stand on the Upper West Side this evening, you might hear on the chilly breeze a great collective moan of sorrow. This is not the mass lamentation of a care-worn and inquiring people begging for forgiveness and inscription into the Book of Life for one more year. No, this is the full-throated wail, thousands strong, of those who have gathered at Madison Square Garden on 33rd Street–oh, do let’s call it “Toity-Toid” just for tonight–to see the first of the two final concerts ever given by Barbra Streisand, our one true Jewish saint. These are indeed the Days of Awe. Read More

25 Classic Nancy Grace (Getty Images)

Did Nancy Grace, TV Crimebuster, Muddy Her Myth?

By Rebecca Dana

[Ed. note: This article was originally published on March 6, 2006.]

Every crime-fighting superhero has a creation story. Nancy Grace, the prosecutor turned breakout star at CNN Headline News, has a particularly moving one. As she tells it, in the summer of 1980, she was a 19-year-old college student in small-town Georgia, engaged to Keith Griffin, a star third baseman for the Valdosta State University Blazers. The wedding was a few months away. Read More

25 Classic Gail Sheehy (Getty Images)

Life Is What You Make It

By Gail Sheehy

[Ed. note: This article was originally published on July 1, 2008.]

June 24, 2008

Dear Friends of Clay,

It is said that people die the way they live. Knowing Clay as you do, you will probably not be surprised by the story I want to share with you. In the past week, as he approaches the final deadline of his life, Clay’s life force returned with gusto. Read More

25 Classic Tom Wolfe (Getty Images)

Tom Wolfe on the City of Change

By Tom Wolfe

[Ed. note: This article was originally published on December 17, 2001.]

Has it been duly recorded that everything in New York changed just before Sept. 11? Granted, it’s hard to get the picture here in the Afghan glare of the TV set, but it looks like this: Read More

25 Classic New York City skyline (Getty Images)

City of Ambition Will Rise From Ashes of 9/11

By Clay Felker

[Ed. note: This article was originally published on February 4, 2002.]

As the head of Chase Manhattan Bank, a great international power, David Rockefeller’s appointment book filled up as much as a year in advance. So I was surprised to receive an invitation to lunch with him at his headquarters near the southern tip of Manhattan. Read More

25 Classic Shmomo-Erectus Pride? (Getty Images)

Shmomo Erectus

By Tom McGeveran

[Ed. note: This article was originally published on August 18, 2003.]

“It’s a Gay World After All!” screams VH1 in a press release pumping up their Aug. 18 documentary, Totally Gay . The show, VH1 says, will capture a phenomenon that has built to a fabulous crescendo this summer. “In the early 90′s, the entertainment landscape was a virtual gay wasteland,” the promoters scold. “Fast forward to 2003, where ‘gay is the new black.’” Read More

25 Classic (Getty Images)

Rrrowl! Beware Cougar’s Young Niece, the Cheetah

By Spencer Morgan

[Ed. note: This article was originally published on December 1, 2009.]

It was 2:30 a.m. on a school night about a year ago when Seth, Joel and Dana left the party and headed into the rain. The party had been unremarkable, only this time Seth had allowed the open bar to get the better of him. He knew he was completely wasted. What he didn’t know was that a predator was watching his every move. Read More

25 Classic (Getty Images)

Yes, I Flew JetBlue Flight 292

By Alexandra Jacobs

[Ed. note: This article was originally published on October 3, 2005.]

As we passengers joyously disembarked from JetBlue Flight 292 on the evening of Sept. 21, 2005, one of Los Angeles’ gorgeous toxic sunsets was illuminating the kindly, ruddy, handsome faces of the suddenly superfluous but very welcome emergency personnel gathered on the tarmac. They all looked like 1940’s movie heroes reduced to skycap duty (my fully loaded red carry-on was but a piece of Barbie luggage in the beefy hands of one Dana Andrews–esque fireman). Read More

25 Classic Hello, Times Square!

See Ya, East 64th St.! 17 Giddy Years In Dotty Squalor

By Peter W. Kaplan

[Ed. note: This article was originally published on November 8, 2004.]

For 17 years, since The New York Observer entered city life in 1987, it has existed within a red brick and white-marble-stepped townhouse on East 64th Street. When I entered for the first time, I had an enzymatic sensation I think was shared by many people who worked here-some to their pleasure, some to their horror: I’m home. I’d worked at plenty of publications in New York, but never in a house. As Polly Adler, the great Manhattan bordello madame of the 1920′s said of her own business, a house is not a home. Except in our case. Read More