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‘School of Rock’ Cast Reunites for Caitlin Hale and Angelo Massagli’s Wedding

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‘School of Rock’ Cast Reunites for Caitlin Hale and Angelo Massagli’s Wedding

Angelo Massagli and Caitlin Hale met as co-workers. They were 10 years old.

The pair, former child actors, were both cast in the 2003 film “School of Rock” in which Jack Black plays a substitute teacher who creates a rock band out of his classroom of musically gifted elementary-aged prep schoolers. Ms. Hale’s character was a braided pigtail-wearing backup singer named Marta. Mr. Massagli played Frankie, who was part of the band’s peewee security detail.

Mr. Massagli recalled being spontaneously asked to sing at his audition for the film in New York City. He was nervous to perform after Ms. Hale, who had just impressed the production team with her voice, including a rendition of “Everything’s Coming Up Roses” in which she changed the lyrics to be about the film’s director.

“I was like, ‘wow, that girl’s really, really, really something else,’” Mr. Massagli said. He performed the only song he knew the words to at the time: “Crazy Train” by Ozzy Osbourne.

A year later, the pair and the other children cast in the film spent several months shooting the movie in New York. The group bonded quickly, Ms. Hale said, attending real school on set and having meals at Benihana. Mr. Black, the film’s adult star, would eat lunch with the group and play games between scenes. Their moms, often present on set, also became close during this time.

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Back then, there was not even a hint of a youthful crush between them, the couple said. After the film’s release, the cast stayed in touch through a long-running group chat.

Eventually, Mr. Massagli and Ms. Hale both left show business to pursue other careers.

Ms. Hale, now 33, has a bachelor’s degree in journalism and public relations from Arizona State University. Mr. Massagli, 32, graduated from Northeastern University, majoring in English. After completing their undergraduate studies, both Mr. Massagli and Ms. Hale pursued further degrees, coincidentally both finding their way to schools in Florida, where they reconnected in 2018.

At the time, Mr. Massagli was a law student at the University of Miami. Ms. Hale was completing a bachelor’s of science and a master’s degree in health leadership at Nova Southeastern University in Fort Lauderdale. (Both eventually graduated from their respective programs. Mr. Massagli is now a lawyer for TikTok where he works as music product counsel. Ms. Hale is an Ob/Gyn sonographer.)

After realizing their proximity, the pair got lunch and caught up. They even sent a selfie to their moms.

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“We thought that was kind of it,” Mr. Massagli said. “But we just kept grabbing dinners and going out for the weekends. We were like, ‘something’s brewing here.’”

On an early date, Ms. Hale recalled going to the bathroom and returning to the restaurant table to find Mr. Massagli had ordered coconut cake for dessert, a flavor she’d previously mentioned was one of her favorites. She appreciated his close listening, she said.

Their relationship moved quickly, the years spent as childhood friends offering a strong foundation.

“Even though it wasn’t romantic, that familiarity we had and our families had when we were younger, really cut through some of those early relationship hurdles,” Mr. Massagli said.

“I knew very early,” Ms. Hale said. “I actually said to one of my close friends, I remember being in an Uber on the way down to Miami one weekend and we were going out and I was like, ‘I think I’m gonna marry this guy.’”

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The first time Mr. Massagli told Ms. Hale he loved her his exact words were, “I think I love you.”

“You think?!” Ms. Hale exclaimed in pseudo-exasperation.

Later that year, Mr. Massagli offered up his home as a short-term stay to help Ms. Hale cut down on the commutes between her home in Fort Lauderdale and a residency program in Miami. He was going out of town for a week and gave her a key and permission “to crash.” By the time he returned, she had moved in.

The couple moved to Brooklyn in 2019 and got engaged in June 2023 at the Metropolitan Museum of Art. Mr. Massagli proposed in front of the Temple of Dendur, the light-filled gallery featured in the film “When Harry Met Sally…” Dinner at Nino’s, an Upper East Side Italian restaurant, and champagne at the Carlyle followed. Upon hearing the news via FaceTime, Mr. Massagli’s mother burst into tears.

For their wedding, the couple knew they wanted to “go all out,” Ms. Hale said. On Jan. 4, they celebrated their wedding at Park Château Estate & Gardens, a Versailles-like wedding venue in East Brunswick, N.J. (They had previously made things legal on Aug. 30 at Brooklyn Borough Hall. Waldo Ramirez, a staff member of the City Clerk’s Office, officiated.)

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Ms. Hale started her day at 8:30 a.m. getting glammed up for the evening celebration. Ms. Massagli had a more leisurely morning, including a massage.

The couple, who now live in Long Branch, N.J., had read private vows to each other the night before the main event. Ms. Hale’s father, Gary Hale, officiated a brief ceremony before the party began.

Binge more Vows columns here and read all our wedding, relationship and divorce coverage here.

Guests were then whisked into cocktail hour where they sipped the couple’s signature drinks: a Bellini for her and a dirty martini with blue cheese olives for him. The venue was decorated with exclusively white flowers and, per Ms. Hale’s vision, many, many white candles.

For the reception, Ms. Hale changed into a pair of custom-made rhinestone-studded, thigh-high Berta boots that peeked out of the slit of her strapless gown.

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“Once I saw those boots, I was like, I need to do whatever I can to make sure to have those,” she said. “The dress can follow.”

The couple entered the reception to “Through the Wire” by Kanye West, which transitioned into Chaka Khan’s “Through the Fire” for their first dance. They asked their D.J. to play songs that felt like “if Studio 54 never closed,” Mr. Massagli said. A live saxophone player roamed the party riffing over the piped-in music.

During “Edge of Seventeen” by Stevie Nicks, the duo danced with their castmates from “School of Rock,” a nod to a bar scene from the film. Nine cast members were there, as well as more than a dozen of the actors’ parents and siblings. (Jack Black politely declined, citing an ongoing film project, but “was so nice and generous with his words and definitely commemorated it privately,” Ms. Hale said.)

Not wanting to throw off the party vibe, at one point Ms. Hale and Mr. Massagli stepped away for a private cake cutting where they fed each other “delicate, small bites,” Ms. Hale said, laughing.

Ms. Hale recalled another moment on the dance floor with her fellow former “School of Rock” backup singers as a “time capsule moment.”

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“We were just dancing together to some old-school disco and then there was some sort of ad lib in the song and we all just hit it,” she said. “We looked at each other and we’re like, ‘That just happened. We still got it.’”


When Jan. 4, 2025

Where Park Château Estates and Gardens, East Brunswick, N.J.

The Family Stone Both the bride and groom wore sentimental rings. Mr. Massagli’s wedding band was passed down from his grandfather. “He’s big Ang, I’m little Ang,” Mr. Massagli said. Ms. Hale’s oval diamond engagement ring was a repurposed ring from her mother.

Late Night Snacks In addition to a three-tiered wedding cake — each tier was a different flavor — guests were served cannoli on the dance floor. When the night ended, guests walked out past a food truck handing out McDonald’s.

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Bill Maher is getting the Mark Twain Prize after all

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Bill Maher is getting the Mark Twain Prize after all

Satirist Bill Maher is this year’s recipient of the Mark Twain Prize for American Humor. Maher will receive the award at the Kennedy Center on June 28th. The show will stream on Netflix at a later date.

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Bill Maher will be receiving the Mark Twain Prize for American Humor after all.

There’s been some confusion about whether the comedian and longtime host of HBO’s Real Time with Bill Maher would, indeed, be getting the top humor award. After The Atlantic cited anonymous sources saying he was, White House press secretary Karoline Leavitt called it “fake news.” But today the Kennedy Center made it official.

“For nearly three decades, the Mark Twain Prize has celebrated some of the greatest minds in comedy,” said Roma Daravi, the Kennedy Center’s vice president of public relations in a statement. “For even longer, Bill has been influencing American discourse – one politically incorrect joke at a time.”

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Is President Trump, chair of the Kennedy Center’s board, in on the joke?

Maher once visited Trump at the White House and he tends to be more conservative than many of his comedian peers but after their dinner Trump soured on Maher, calling him a “highly overrated LIGHTWEIGHT” on social media.

Maher’s acerbic wit has targeted both political parties and he’s been particularly hard on Trump recently, criticizing his decisions to wage a war with Iran and his personnel choices.

“Trump said, ‘when oil prices go up, we make a lot of money.’ Um, who’s ‘we?,’” Maher said in a recent monologue.

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Past recipients of the Mark Twain Prize include Conan O’Brien, Dave Chappelle, Jon Stewart, Julia Louis-Dreyfus, Tina Fey, Eddie Murphy and Carol Burnett.

In a statement released through the Kennedy Center, Maher said, “It is indeed humbling to get anything named for a man who’s been thrown out of as many school libraries as Mark Twain.”

Maher will receive the Mark Twain Prize at the Kennedy Center on June 28. The show will stream on Netflix at a later date.

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What European Luxury Can Learn From American Fashion

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What European Luxury Can Learn From American Fashion
This week on The Debrief, BoF’s Diana Pearl explains why brands like Coach, Ralph Lauren and Tory Burch are outperforming many European luxury houses — and what their turnarounds reveal about pricing, product, retail and long-term brand building.
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Suit asks court to force Trump administration to use ‘The Kennedy Center’ name

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Suit asks court to force Trump administration to use ‘The Kennedy Center’ name

Workers react to the media after updating signage outside the Kennedy Center on Dec. 19, 2025, in Washington, D.C.

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Rep. Joyce Beatty of Ohio is asking a federal court in Washington, D.C., to force President Trump and the board and staff of the Kennedy Center to revert to calling the arts complex The John F. Kennedy Center for the Performing Arts.

The motion, which Beatty filed on Wednesday, asks a federal circuit court judge to reverse the Trump administration and the center’s current board and staff’s decision to call the complex “The Trump-Kennedy Center.”

In the filing, Beatty’s attorneys wrote: “Can the Board of the Kennedy Center — in direct contradiction of the governing statutes — rename this sacred memorial to John F. Kennedy after President Donald J. Trump? The answer is, unequivocally, ‘no.’ By renaming the Center — in violation of the law — Defendants have breached the terms of the trust and their most basic fiduciary obligations as trustees. Shortly after President John F. Kennedy’s assassination, Congress designated the Kennedy Center as the ‘sole national memorial to the late’ President in the nation’s capital.”

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In a statement emailed to NPR Thursday, Roma Daravi, the vice president of public relations for the Kennedy Center, wrote: “We’re confident the court will uphold the board’s decision on the name change and the desperately needed renovations which will continue as scheduled.” NPR also reached out to the White House for comment, but did not receive a reply.

In December, White House press secretary Karoline Leavitt announced that the complex would heretofore be called “The Trump-Kennedy Center.” Although the new moniker was never approved by Congress, the Center’s website and publicity materials were immediately updated to reflect the administration’s chosen name, and the same day as Leavitt’s announcement, Trump’s name went up on the signage of the complex’s exterior, over that of the slain President Kennedy.

Later that month, Rep. Beatty who serves as an ex-officio member of the Kennedy Center’s board of trustees, sued Trump, members of the Kennedy Center board appointed by Trump, and some ex-officio members, arguing that the complex’s name had been legislated by Congress in 1964. Wednesday’s motion is part of that lawsuit.

In a press release sent to NPR on Wednesday, Rep. Beatty said: “Donald Trump’s attempt to rename the Kennedy Center after himself is not just an act of ego. It is an attempt to subvert our Constitution and the rule of law. Congress established the Kennedy Center by law, and only Congress can change its name.”

For many patrons, artists and benefactors of the Kennedy Center, the name change was the last straw in politicizing the performing arts hub. Following the White House announcement of the new name, many prominent artists withdrew planned performances there, including the composer Philip Glass (a Kennedy Center Honors award recipient, who received his prize during the first Trump administration), the famed Broadway composer and lyricist Stephen Schwartz and the 18-time Grammy-winning banjo master Béla Fleck.

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The Washington National Opera (WNO), which had been in residence at the Kennedy Center since 1971, also severed its ties in January after ticket sales dropped precipitously. Earlier this month, WNO artistic director Francesca Zambello told NPR, “We did try as best as we could to encourage [the patrons] that we are a bipartisan organization, but people really voted with their feet and with their pocketbooks. And so we realized that there was really no choice for us.”

On Monday, a coalition of eight architecture and cultural groups also sued Trump and the Kennedy Center board in federal court over the complex’s scheduled closing in July for unspecified renovations. Their suit seeks to have the White House and board members comply with existing historic preservation laws, and to secure Congressional approval before moving ahead with the renovation plans.

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