Here’s My Number, So Call Me Jenny: Carly Rae Jepsen and J.Lo Headline amfAR’s Inspiration Gala

Kenneth Cole and Jennifer Lopez.

Kenneth Cole and Jennifer Lopez.

Honestly, Shindigger had intentionally skipped the first two hours of cocktails for amfAR’s fourth annual Inspiration Gala in NYC. We knew we were in for a very long one—featuring some star-powered and cash-flush heavy hitters—because producer/promoter Josh Wood never skimps on his big-budget events.

Upon arrival, we stumbled into a vacant seat in The Plaza’s Palm Court just in time to catch the end of a 54-look, military-inspired runway presentation. Across the catwalk, Ireland Baldwin giggled with delight as the meat in a Dsquared2 sandwich (the bread being twin designers Dean and Dan Caten). In another section, Iman tee-heed next to Paul Wilmot as Derek Blasberg presided over a cluster of models composed of Eniko Mihalik, Lindsey Wixson and Leigh Lezark.

“Who knew camouflage was so sexy?” asked Uma Thurman after the assembled parties had unhurriedly crept upstairs to their tables, plated with a starter of beet ravioli, chèvre and mezze arugula.

“No wonder people join the military,” she continued. “But it would be tough to hide some of those outfits.” Ms. Thurman then spoke about the Foundation for AIDS Research’s amazing work and how its Inspiration events have raised more than $10 million. This evening, amfAR would be honoring Valentino Garavani, Jennifer Lopez and Alan Cumming.

Shindigger reached for a second glass of rouge and did an eye-twirl around the fashion-dominated room: Thom Browne was next to Lorenzo Martone at one table, Shala Monroque was at another, and there was an attractive entourage from Calvin Klein Collection, including Hanneli Mustaparta, Dree Hemingway and creative director Italo Zucchelli.

From the podium, Ms. Thurman was wrapping up her opener: “Liza Minnelli is in the house, Iman is here, and believe me, Ms. Carly Rae Jepsen will bring down the house!”

“We’ll be the judge of that,” one twink snapped within earshot.

Next up, Kenneth Cole, chairman of the amfAR board, took the stage. “What arguably launched her career,” the designer said of Ms. Thurman, after giving his gal pal a kiss on the cheek, “was Pulp Fiction and then Kill Bill 1, 2 and now 3!”

Was that confirmation that the on-again, off-again rumors about a trilogy are now confirmed? The crowd sure thought so, hollering with delight.

As Shindigger dove into some vegan creation and the dressed-to-kill carnivores all around us carved up roast lemon chicken, Ricky Martin delivered a congratulatory video message from Australia to his amiga J.Lo. And then larger-than-life fashion icon André Leon Talley presented Ms. Lopez, who wore a body-hugging Tom Ford gown and Harry Winston diamonds, with her plaque.

Because Mr. Valentino was unavailable to receive his award—probably tanning in the Mediterranean with Giancarlo—Iman accepted on his behalf.

Things got saucier when amfAR ambassador Liza Minnelli careened to the lectern to present Mr. Cumming with his award, drawing a standing ovation.

Gooooodeeeeevening!” she announced in her Broadway boom. “I have the pleasure and honor of presenting an award to a man who is not only one of the most eclectic talents, but he is also the best damn cabaret partner I have ever had.”

The gala’s live auction was undoubtedly a highlight. An authenticated Warhol “Cow” serigraph went for $25,000. Ms. Lopez created a stir when two patrons coughed up $90,000 each for the privilege of accompanying her to L.A. when she receives her star on the Hollywood Walk of Fame, as well as on a red-carpet date sometime this year.

“I’m a good red-carpet date,” she purred.

Eventually, pop junkies crowded around the stage as Ms. Jepsen, the Canadian pop sensation, belted out her hits. As delightful as hearing “Call Me Maybe” for the zillionth time was, Shindigger reloaded our wine for fear of a harsh reaction. “Have some more wine,” a familiar face suggested, noting Shindigger’s grimace.

One step ahead of you, darling.

Afterward, Shindigger made a beeline for the Macbeth actor.

“Were you having fun tonight? Did you get to mingle?” we asked

“I did Macbeth tonight,” Mr. Cumming responded in his Southern Highlands Scottish accent. “Then I just came here. It was fun to not be weeping and wet and covered in blood.”

“Are you going to the after-party?”

“Hell yeah!”

See you there, we thought, before asking him about his outfit.

“I’m wearing a double mesh shirt,” he said, showing off his cotton printed blazer and navy mesh dress shirt.

Always one to cause a stooshie.

Shindigger then guzzled down a final flute of bubbly before scrambling into a car bound for The Standard at the High Line. En route, we bumped into Mr. Cole.

“I was just so proud,” he said. “We celebrate how far we’ve come, recognize how far we still have to go, and everyone leaves knowing that they had a good time.”

And there were good times still ahead. Once Shindigger was safely at the Top of the Standard, dirty gin martini in hand (gin after wine = just fine!), we asked the gala’s deejay and violinist duo Mia Moretti and Caitlin Moe what the highlight of their night had been.

“Liza!” Ms. Moretti blurted over the dance beats.

“Jennifer Lopez! J.Lo is my mother!” Ms. Moeenthused.

“Where are you partying,” we wondered, “at Le Bain or Boom Boom with Dean Caten?”

“All day he’s been tricking me,” replied Ms. Moretti. “He’s been calling, baiting me with hamburgers, just to get me to go somewhere. So apparently there are hamburgers on the roof, so we must go!”

And the carnivores partied on.