Katie Holmes and Mayor Michael Bloomberg at The New York Observer's 25th anniversary party.

Last Thursday evening at New York’s perch of power dining, the Four Seasons Restaurant, billionaires could be found clinking glasses with politicians, actors could be seen rubbing shoulders with news correspondents, and throngs of notable wordsmiths quaffed copious amounts of liquor at The New York Observer’s 25th anniversary soiree.

“I think this is the best collection of New Yorkers I’ve seen in 20 years!” effused Ronald Perelman, who leered lustily at our highball glass.

“Can I ask you one question?” he continued. “Where’s the bar?”

It’s thataway, just behind Katie Couric, we assured the business tycoon. Or if he preferred, he could hit the bar on the other side of the restaurant’s famous pool room, where Harvey Weinstein had posted up and Spike Lee, who declined to take off his puffy coat, had helped himself to the generous spread of gourmet goodies before chatting up Katie Holmes and Donald Trump.

(Sadly, Shindigger caught only the tail end of that conversation. Mr. Lee saying to Mr. Trump: “Well, that’s one thing we can agree on.”)

Observer editors past and present—Peter Kaplan, Elizabeth Spiers and Ken Kurson—circled the room, while publisher Jared Kushner greeted guests with wife Ivanka Trump at the door. And from the worlds of business, politics, entertainment, fashion and beyond, the stars just kept pouring in. Even Mayor Michael Bloomberg was impressed with the turnout. “The Observer does throw a hell of a party,” he said in his opening remarks, before dubbing attendee Cory Booker “the handsomest mayor in America—west of the Hudson River.”

Here came Terry McDonell and Danny Strong and Jay McInerney and Audrey Gelman and Larry Gagosian and Ray Kelly and Joel Klein and George Pataki and Eric Schmidt and Kevin Ryan and—oh my!—Rupert Murdoch.

We just had to talk to Rupert Murdoch

“Mr. Murdoch? Mr. Murdoch?” Shindigger beckoned.

“What?” said the cantankerous billionaire, walking right on by with wife Wendi Murdoch.

“Can we ask you a few questions, sir?”

“No!” barked Mr. Murdoch, before making a dramatic swat in our direction. Shindigger agilely ducked for safety, silently chuckling at the news baron’s aversion to the press.

In no time at all, we found friendlier prey. “Someone from The Observer already observed me,” said Broadway favorite Christine Baranski, who was chatting with fashion consultant Fern Mallis under the floral protection of one of the poolside trees.

“New York is just the coolest city, and I love the fact that this paper really makes New York seem cool,” Ms. Baranski said. “The Observer touches on the sophistication and fun of the city. I just like the tone of it.”

Just then, we re-encountered Mr. Perelman, who had been paired with a cocktail, and who had his own take on The Observer. “The only bad moment I ever had was when they wrote a story about a little synagogue,” Mr. Perelman said, referring to Chloé Malle’s prickly 2010 article about the billionaire’s lavish private synagogue.

“I wish they didn’t, but they did, so that’s the end of it,” he said. “I still love The Observer, even besides that.”

Very gracious, we thought, bumping then into Observer alum George Gurley, with whom we had pre-gamed earlier in the evening at Jean and Martin Shafiroff’s glitzy Saint Patrick’s Day cocktail party. The suavely fuddled Mr. Gurley made the perfect VIP-fixer for Shindigger when PR maven Peggy Siegal was hand-holding elsewhere.

“He does Shindigger, he’s trustworthy,” Mr. Gurley assured José “Pepe” Fanjul, the president of Fanjul Corp. and Florida Crystals Corporation.

“I think this is the best event!” exclaimed Mr. Fanjul’s Carolina Herrera-clad wife, Emilia Fanjul.

We danced past the couple then to catch up with model Hilary Rhoda, who was getting a kick out of the bash.

“Oh, it’s a great party!” she said, holding a plate of Christian Albin’s Italian gourmet cibo. “I love the room, it’s gorgeous. I love the band. Obviously getting into the food situation.”

Ms. Rhoda, also dressed in a Carolina Herrera creation, had just returned from the runways of Paris, where she had walked for Céline. “Now I’m back and on photo shoots,” she said.

Photorealistic artist Chuck Close was also taking advantage of the buffet.

“I love The Observer almost in spite of myself,” he said. “At first it was a guilty pleasure, and then one day they endorsed Mitt Romney. I almost canceled my subscription. What were they thinking?”

What brought you back onboard, we wondered?

“When I go to Europe and can’t read you, I get really upset,” he confessed. “It went from being a guilty pleasure to a real pleasure.”

A cocktail later, we found ourselves yelling: “Ms. Herrera, we saw you at the School of American Ballet’s Winter Ball, and you were dancing!”

Shindigger had never witnessed her quite so zippy.

“Yes, I know. I’m South American,” Carolina Herrera retorted sassily.

Cuchi-Cuchi!

Back to the bar we traipsed.

“Do you have a white wine or champagne?” Padma Lakshmi pressed a barman.

“Rosé or brut?” he asked.

“Brut,” the foodie stated assuredly.

Ms. Lakshmi wanted to know our thoughts about her Blossom Ball. “Did you have fun?” she asked.

“We did, “Shindigger said.

“I’m glad!” she said. And then the Maison Martin Margiela-wearing TV host told us about the previous day, which she had spent in Albany: “I was recognized by the State Senate. Every State senator was there, because it’s budget time,” she dished, lowering her voice to a serious, husky tone. Though she lost us at “budget.”

When the band was replaced by DJ Chelsea Leyland’s turntables, things had officially strayed, and Shindigger was impressed (and a tad disappointed) that not a single sloshed attendee plummeted into the white marble pool. Cases in point: when perpetually grabby Four Seasons proprietor Julian Niccolini began frisking two attractive slabs of meat, offering to shower them with pricey pours of Bordeaux. Or when Gawker founder Nick Denton resorted to flirting with a pride of hungry tech lionesses, having already refused to be photographed with Mr. Murdoch because “it’s too obvious.”

Shindigger sidled up to the bar for last call with Ashleigh Banfield of CNN and Fox News’s Kimberly Guilfoyle.

“We’re together,” Ms. Banfield joked about their warring media outlets. “I’ve known her for eight years. We use to work at Court TV together.”

“Did you see Rupert Murdoch? He didn’t want to talk to us,” we bemoaned.

“Because I work at CNN, he didn’t want to talk to me, either,” said Ms. Banfield.

“No, he’s great! God bless him!” Ms. Guilfoyle cut in, right on cue.

As Rihanna’s “Diamonds” thundered over the speakers, Ms. Banfield revealed that she had gotten a smooch from the Newark mayor.

“We had a Cory Booker sandwich,” swooned Ms. Guilfoyle.

As things were wrapping up, at least one guest took on a reflective air. Mr. Close told us that he was overwhelmed by the turnout and notable faces. “I’ll make sure to be at the 50th anniversary,” he promised. “I’ll be 98.”

Shindigger likes a man who can forecast that far ahead—or, for that matter, with any type of math skills.

Here’s to the next 25 years!