‘School of Rock’ Child Stars Get Married 22 Years Later

It feels like Caitlin Hale and Angelo Massagli were simply meant to be. When they were cast in the 2003 comedy School of Rock starring Jack Black, they were just kids. Little did they know that two decades later they’d tie the knot in an elegant winter wedding at the Park Château Estate & Gardens in East Brunswick.

Not only did they end up landing roles in the feel-good film, but they had back-to-back auditions in Manhattan.

Casting directors scoured the country to find the right kids for the movie, which follows a class of private school students who form a rock band thanks to a down-and-out guitarist (played by Black) posing as a substitute teacher. “The fact that we were there in the same city on the same day at the same time is unbelievable to think about,” says Caitlin, who is from New Haven County in Connecticut.

The audition still stands out in Angelo’s mind, who is a Putnam County, New York, native. Caitlin went in right before him and “started belting show tunes and she was so good,” he says. “When she walked out, I’m like, ‘wow, that girl is so talented’…I always distinctly remember Caitlin from that day, which I always thought was kind of cool, especially in retrospect.”

While filming in New York City, Angelo, who was 10 years old, and Caitlin, who was 11, had the best time with their fellow child castmates. (Caitlin was cast as Marta “Blondie,” a backup singer for the band, and Angelo played Frankie “Tough Guy,” the band’s security guard.) They’d all grab hot chocolate in the morning before heading to the set. During downtime, the group would do schoolwork, play video games and have snowball fights. They have fond memories of outings to Dylan’s Candy Bar and Madame Tussauds wax museum. The group’s favorite spot to eat was Benihana for hibachi.

“We spent so much time together and really formed such a strong bond,” says Caitlin. “It was such a great time to be able to do that with so many kids who we’re still such close friends with.”

A School of Rock group chat among many of the cast members has been going strong for years.

“We always just stay in touch with each other and keep each other updated on what everyone’s doing,” says Angelo. (Prior to School of Rock, Caitlin had a guest role on the soap opera All My Children. Angelo, meanwhile, played Bobby Baccalieri Jr. on The Sopranos from seasons four to six, both during and after School of Rock.)

Fast forward to 2017 and Angelo was attending law school at the University of Miami. One day, Caitlin dropped a text in the chat asking if any of her former castmates were living in Florida. She was getting her master’s in health care leadership at Nova Southeastern University in Fort Lauderdale and wanted to reconnect with her friends. Angelo piped up in the group chat to say that he was also studying in the Sunshine State and would be down to get together.

The pair grabbed lunch, caught up on life and snapped a selfie that they sent to their moms, who knew each other from their time on set.

From there, the pair kept communicating. “I would tell Angelo about the cases I was learning about, and he would share the things he was learning in law school,” says Caitlin. They would meet up on weekends, and their relationship continued to progress. By late 2018, they were an item.

“There was a familiarity having known each other from the movie,” says Angelo, “but at the same time, a lot of time had passed, and we were just totally new people at that point…I think it made things feel organic and real.”

After graduating in 2019, the couple moved to Brooklyn, and in June 2023, Angelo decided to propose.

“I wanted to have a nice classic New York City engagement,” he says. So, he took Caitlin to the Metropolitan Museum of Art. He had a loose plan for the day and figured he’d know the right proposal spot when he saw it.

Once they entered the room that houses the Temple of Dendur, a well-known spot in the museum thanks to a scene in the film When Harry Met Sally, Angelo thought to himself: all right, this is it.

Caitlin was happily surprised. “I had an inkling that it was going to happen soon, but how, when and where—I had no idea,” she says.

To celebrate, they went to dinner at Nino’s 46 on the Upper East Side and grabbed dessert and drinks at the Carlyle hotel.

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Angelo, now an entertainment lawyer for TikTok, and Caitlin, who works as a sonographer and real estate agent in New Jersey, took a few months to celebrate their engagement before they began to hunt for both wedding venues and a new place to live.

The Park Château was the first New Jersey wedding venue that they toured, and they instantly fell in love with the grounds, the food offerings and the convenience of the on-site Château Grande Hotel. “You could tell that they’ve done this so often and so well for so long,” says Angelo. “I felt completely taken care of.”

So, the couple booked the high-end venue right around the same time that they signed a lease for a Long Branch apartment. “We knew that, if we were going to leave Brooklyn, we had to live on the beach—just a total life shift,” explains Caitlin.

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On January 4, 2025, more than two decades after meeting as child actors, the couple said “I do” inside the Park Château’s lovely chapel.

For their winter wedding, they wanted to incorporate a lot of candlelight and white flowers. The Park Château still had its holiday decor on display, which further enhanced the couple’s vision. Caitlin describes the vibe they were after as “very clean, modern, a lot of glamour.”

Speaking of glamorous, Caitlin rocked thigh-high sheer, bedazzled Berta boots for the reception. She had three fittings just for the footwear. “They were more high maintenance than the dress,” a sleek strapless gown also by Berta, she says. Angelo looked dapper in a black suit by Cad & The Dandy.

Angelo, 32, and Caitlin, 34, wanted their 150-guest reception to be one to remember.

“We definitely wanted people on the dance floor for the whole night,” says Angelo. “We wanted it to feel like Studio 54 never closed.” Their DJ, Raul of Elite Sound Entertainment, played everything from disco to R&B to hip-hop and reggaeton.

Although they no longer perform on screen, entertaining is still second nature for the couple.

“I wanted to make sure that our guests were entertained and there was something for everyone,” says Caitlin. “And I think too, a part of it is like, yeah, we may not be acting anymore, but you still got to put on a show, you know, you got to deliver.”

They had a saxophonist, Sax Man Art, who was “so much fun and engaging with everybody,” says Caitlin. There was a live painter who created a portrait of Caitlin and Angelo during their first dance and also sketched portraits of guests throughout the night. When it was time for dessert, Carrello di Cannoli, better known as the Cannoli Guy, made his way onto the dance floor. “He gets right out there and makes cannolis for people and he is dancing around and it’s just high energy the whole time,” says Caitlin.

Their wedding was also a reunion for many of the School of Rock cast members and their parents. (Jack Black was invited but could not attend.)

The duo made a point to play “Edge of Seventeen” by Stevie Nicks during the reception as “a little wink to School of Rock,” says Angelo. In the movie, Jack Black and Joan Cusack’s characters share a funny moment at a bar as this song plays. When the song came on at the wedding, the cast members who were guests—Z Infante, Brian Falduto, Rivkah Reyes, Joey Gaydos, Cole Hawkins, Robert Tsai, Aleisha Allen, Maryam Hassan and James Hosey—“they all got it immediately,” says Caitlin, as they headed to the dance floor.

Many of the castmates’ parents were also in attendance at the wedding. “Since we were all kids on the set,” explains Angelo, “just as important as us were our moms who were all with us for the months while we were acting.”

As they reflect on their big day, the newlyweds agree that their love story has come full circle.

“We were on the same audition with each other. We got onto this movie with each other, which is so rare. I mean, it’s not easy to get a role at all let alone something like [School of Rock], which was so exceptional in and of itself,” says Angelo. “And it doesn’t really escape me that the whole thing just feels like it was meant to be.”

The School of Rock movie also went on to be developed into a Broadway musical and a TV show. “Just the outpouring of love surrounding this project is unbelievable,” Caitlin says. “And we’re so lucky to have been a part of that.”

But most of all, they feel lucky that the movie brought them together. “To get a relationship out of [this project], and a marriage out of it, and a partner for life,” says Caitlin, “you couldn’t ask for more.”

Wedding Vendors

Venue Park Château Estate & Gardens, East Brunswick Photographer Julian Ribinik Studios DJ Raul Chiriboga of Elite Sound Entertainment Saxophonist Arthur Crichlow III of Sax Man Art Florist & Decor Bespoke Floral Hair Royal Brides by Senada Makeup Glamour by Drita Planner Christie Napurano of The Wedding Plan & Company Bride’s Gown Berta Bride’s Shoes Jimmy Choo (ceremony); Berta (reception) Groom’s Suit Cad & The Dandy Groom’s Shoes Ferragamo Cannoli Vendor Nick D’Anna of Carrello di Cannoli, “The Cannoli Guy” Live Painter/Guest Portraits Hannah Paints Events Cake Calandra’s Bakery Late-Night Food Truck Mobile Delights (candy and McDonald’s)

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