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Drew Barrymore returns to Chicago, a city that ‘changed my life’

More than 20 years after shooting scenes here for “Never Been Kissed,” the actress visits again to honor two CPS educators and tape segments for her daytime talk show.

A CPS educator stands with her husband and Drew Barrymore at a Chicago taping of “The Drew Barrymore Show.”
Art educator Amy Castaneda (center) stands with Drew Barrymore (left), her husband Rob Castaneda (right), and her former students Saturday during the taping of a segment for Barrymore’s talk show at Josefa Ortiz de Dominguez Elementary School.
CBS Media Ventures

In the 1999 comedy Never Been Kissed,” Drew Barrymore played an insecure Chicago Sun-Times copy editor, Josie “Grossie” Geller. A lot has changed since Josie rode the Ferris wheel at Navy Pier with her love interest, but Barrymore said she still relates to the film’s themes of vulnerability and risk.

“I just am always looking for the common thread among human beings,” the Golden Globe winner said. “To me, [Josie] was a perfect comedic outlet and symbol for me to say, ‘We all feel like this inside, man, we all do.’”

Last year, Barrymore revived Josie for her daytime talk show, “The Drew Barrymore Show.” Wearing the iconic pink satin prom dress from the movie, Josie reported on the presidential election for the show’s “Drew’s News” segment. Barrymore said Josie resembled the “goof” and comedic relief she wanted the talk show to offer during the pandemic.

Josie Geller from “Never Been Kissed” in her signature prom dress on “Drew’s News.”
Drew Barrymore reprises her role as Josie Geller from “Never Been Kissed” for a special edition of “Drew’s News,” a segment on her daytime talk show.
CBS Media Ventures

Barrymore returned last weekend to Chicago to film segments for “The Drew Barrymore Show,” which airs at 9 a.m. weekdays on WBBM-Channel 2.

“I’m excited to come back here and feel like I still can be a storyteller,” Barrymore told the Sun-Times. “I’m not here making a movie. I’m glad I’m here making a show that can be about other people.”

In the Chicago segments, Barrymore celebrates two Chicago Public Schools educators, samples some of Chicago’s famous dishes and hosts a “Drew’s News” segment in front of The Bean.

Amy Castaneda is one of the Chicago educators featured in the talk show. Barrymore surprised Castaneda at her school, Josefa Ortiz de Dominguez Elementary School, in Little Village. She was awarded $10,000 at the taping, and the school received $20,000 in STEM-related educational toys from local companies Learning Resources and Hand-2-Mind.

Former students and colleagues filled the school gymnasium on a Saturday to celebrate her as Castaneda accepted the giveaway. “That was really a lot of love in that room, a lot of support, just a lot of meaning behind long-term relationships,” said Castaneda, an art educator for 24 years.

The packed gymnasium at Josefa Ortiz de Dominguez was one of the largest in-person audiences “The Drew Barrymore Show” has had to date. The talk show launched during the pandemic, and producers had to retrofit the audience in its New York studio to comprise a virtual crowd. As COVID-19 restrictions altered the work environment, the show went through several iterations. Barrymore described building relationships with her producers over Zoom.

But a pandemic debut also gave Barrymore the license to move away from the traditional talk show. “In 2019, I didn’t want to make a show that was fully based on celebrity. I was struggling with that world myself,” Barrymore said.

Instead of a focus on celebrity guests, she wanted to bring in human-interest stories like Castaneda’s, scheduled to air on the Nov. 23 episode. (The other teacher segment is planned for the show airing this Friday.)

“There’s a lot of work that goes into being a human being functioning on this planet. And so I wanted to talk about a lot of that stuff,” Barrymore said.

Barrymore has also made her kitchen and culinary adventures the center of the show, bringing on chefs like Rocco DiSpirito and Pilar Valdes. The Chicago trip was no different, with Barrymore trying a hot dog from Jimmy’s Red Hots.

Barrymore said she grew up “under the John Hughes rule” as a fan of the director’s coming-of-age films set in the city’s suburbs. Because of the movies, the California native said she felt like she already knew Chicago and the city’s dynamics before she stepped foot in the city.

During the making of “Never Been Kissed,” she experienced heartbreak in Chicago she didn’t think she would survive. She recalled a fight with a boyfriend in her hotel room and walking around the city “like a corpse” after a breakup. “Never Been Kissed” was also the first movie her production company, Flower Films, produced.

“I feel like I’m coming home to a place that really changed my life,” Barrymore said. “I’m really happy to be here back in Chicago for the first time, getting to really be myself and make a show that can honor everybody else.”