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H. Alan ScottLauren Giella

By H. Alan Scott and Lauren Giella

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This week in culture: royals, retirements and reckonings collide. Princess Diana's revenge dress is heading to auction decades after it delivered the ultimate wardrobe comeback and could fetch millions. Judge Judy is stepping down after 30 years on the bench, passing the gavel to her son. Lady Gaga welcomed her first child, proving Mother Monster is now literal. The culture wars also hit the stage: Jasmine Crockett drew backlash for honoring Chris Brown, and Macklemore was booted from Ed Sheeran's tour for saying Free Palestine. Here's everything you need to know.

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Auctions: The Dress That Said Everything

History has no shortage of iconic dresses, but none rewrote the rules of a royal wardrobe quite like Princess Diana's "revenge dress." On June 29, 1994, then-Prince Charles sat for a televised interview and admitted to his affair with Camilla Parker Bowles. That same night, Diana had already planned her own statement, and it didn't need a single word. She stepped out to an event at London's Serpentine Gallery in a black, off-the-shoulder Christina Stambolian gown, breaking royal protocol that traditionally reserved black for mourning. The message landed instantly: She wasn't going anywhere, and she looked better than fine doing it.

Now, that dress is headed to Sotheby's, set to cross the auction block in New York City this December. While the estimate sits between $150,000 and $300,000, history suggests that number is more of a starting point than a ceiling. In 2023, a Jacques Azagury gown Diana wore just twice sold for $1.15 million. Given that this is the dress that basically invented "revenge dressing" as a concept, and the cultural moment it captured has only gotten bigger with time, it would be a surprise if this one didn't blow past the high end too.

Order in the Court, One Last Time

For the past 30 years, Judith B. Sheindlin, better known as Judge Judy, has been a fixture on our televisions, doling out judgment on everything from sibling squabbles to society's biggest debates. TV's favorite judge is stepping down from the bench when this season of her show ends in October. "I'm retiring from in front of the camera," Sheindlin announced on Good Morning America, sitting beside her son, Adam Levy. He was there for a reason: she's not fully hanging up her robes, she's just trading the gavel for a producer's chair on Levy's new show, Adam's Law. Can Levy fill those shoes? Only time will tell. But one thing is certain: Nobody did it like Judge Judy, and television will feel a little less honest without her.

Celebrity: Mother Monster Delivers

Lady Gaga is (literally) Mother! Cue the baby talk puns. The pop icon welcomed her first child with fiancé Michael Polansky.

Gaga, who just wrapped her Mayhem Ball tour in April and has been engaged to Polansky since 2024, took some well-deserved time off. But she recently surprised fans when she was photographed while on a walk with a newborn, sparking well wishes and some incredible memes online.

The Joker 2 star told Stephen Colbert on The Late Show in 2025 that she wanted her next starring role to be a mom. Her new offspring, Rose, has already become the most iconic Little Monster.

Politics: Rep. Jasmine Crockett Is on the Chris Brown Campaign Trail

Jasmine Crockett is being weird. The representative from Texas is facing backlash for honoring the career of R&B singer Chris Brown, a convicted abuser, at his concert in Arlington, Texas.

While onstage at Brown and Usher’s “R&B Tour,” Crockett said she wanted to celebrate the impact of Brown’s career on culture and document this moment of “Black joy” in the Congressional Record.

Crockett recently lost the Democratic primary for U.S. Senate in Texas to state Rep. James Talarico, who is running against Republican Ken Paxton in one of the most consequential midterm races. But instead of spending her time campaigning for the Democratic nominee, she’suplifting a man with multiple arrests and allegations of assault and abuse.

It’s often difficult for fans to separate the art from the artist—but for those who remember seeing photos of Rihanna after she was assaulted by Brown in 2009, it becomes easier. Brown’s record includes a felony assault conviction, multiple arrests and several accusations of physical and sexual abuse. He is currently awaiting sentencing after pleading guilty in connection with a 2023 London nightclub brawl.

This is especially odd for Crockett, who spoke out on behalf of Jeffrey Epstein survivors and likened Americans’ relationship with the Trump administration and the Supreme Court to “an abusive relationship.” For many, her gesture seems, at best, unnecessary, and at worst, hypocritical and disrespectful to victims of abuse. If she’s going to be a sore loser, at least don’t stump for the Chris Brown redemption tour.

Concerts: Macklemore Ouster Sparks Walkouts

Who would’ve thought the “Thrift Shop” guy would be the bastion for free speech in 2026? Macklemore (whose real name is Ben Haggerty) is making headlines after he was kicked off the U.S. leg of Ed Sheeran’s Loop Tour for his pro-Palestinian message. His “Free Palestine” rhetoric drew pushback from stadium owners, including Gillette Stadium owner Robert Kraft, who Macklemore said gave Sheeran’s team an ultimatum: Cut the Seattle-born rapper or find another venue.

Kraft said the rhetoric was “deeply offensive and hurtful” to the Jewish community. Macklemore, for his part, maintains support for people in Gaza and the West Bank, while arguing that criticism of Israel should not be interpreted as criticism of Jewish people.

In an Instagram statement, Sheeran said he respects Macklemore, is “appalled by the conflict between Israel and Palestine” and condemned war.

Although Sheeran attributed the decision to fire Macklemore to the tour promoters, that didn’t stop his remaining opening acts, including Finneas and Danish band Lukas Graham, from dropping out of the tour in solidarity.

Sheeran defends private activism and his choice to keep his show a “sanctuary.” But he broke his original silence on tour to call the situation in Gaza "unjustifiable."

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