After nearly four decades, one of Drew Barrymore’s most iconic fashion moments resurfaced in an unexpected place: the front row of her own talk show.
The moment took place during a taping of The Drew Barrymore Show in New York City, when Barrymore spotted an audience member wearing a black mini dress with purple rosettes along the neckline.
The look immediately caught the host’s attention, stopping her mid-entrance, as it looked remarkably similar to the one she unveiled at the 61st Academy Awards on March 29, 1989.
A fan surprised Drew Barrymore by attending her talk show in a black mini dress that paid homage to her iconic 1989’s Oscar look
“Do you know that I have a history with this dress?” Barrymore asked, walking over to the audience member as cameras rolled.
The woman, who introduced herself as Ruby, quickly confirmed she knew exactly what she was wearing.
“I do,” Ruby said, explaining that she and her mother are “big vintage collectors.” She added that the dress originally belonged to her mom in the 1990s.
“I like to collect a lot of pieces that people wear,” she continued. “This is my homage to you today.”
The actress was stunned.
“I’m so honored!” she exclaimed. “I saw you when I walked in, and I was like, ‘God, that looks like the Betsey Johnson dress I wore to the Oscars.’”
Barrymore was referring to the black cotton off-the-shoulder Betsey Johnson mini dress with two purple rosettes she famously wore to the 61st Academy Awards in 1989.
She was just 14 years old at the time and attended the ceremony with fellow child star Corey Feldman, who was her boyfriend at the time.
The dress brought back memories of a simpler, more innocent time in Barrymore’s life
Barrymore went on to reflect on her iconic Oscar’s look.
“I didn’t have the money, I didn’t have the resources, I didn’t have a stylist,” she told the audience. “So I grabbed my Betsey Johnson off the rack at my house and I wore that to the Academy Awards.”
At the time, the dress felt, in her opinion, noticeably out of place.
The dress was designed by Betsey Johnson, who by the late 1980s was already known for deliberately rejecting red-carpet formality.
Her designs favored playfulness, youth, affordability, and rebellion over couture polish. At the time, Johnson was associated with downtown New York fashion and was openly critical of the elitism of high fashion.
“I loved it!” Barrymore added, laughing. “But I remember getting there and seeing people in such designer duds, and I remember thinking, ‘Oh, I’m very underdressed. I’m wearing a cotton Betsey Johnson dress. Whoops!’”
She estimated the dress likely cost around $65, a far cry from the couture gowns surrounding her that night.
The actress had previously spoken about that night when Corey Feldman, her boyfriend at the time, appeared on her show
The moment wasn’t the first time Barrymore had reflected on that particular Oscars night.
In 2023, Feldman appeared as a guest on her show, where the former couple reminisced about their teenage romance and attending the Academy Awards together.
During the conversation, Barrymore and Feldman spoke about how unprepared they were for the level of scrutiny and spectacle surrounding the event. Feldman described the night as overwhelming.
The two were together for roughly a year before breaking up around April 1990.
Seeing the dress worn by a fan as a deliberate tribute on her show brought a flood of memories back to the actress.
“I’m just so excited to be sharing in this moment with you, Ruby,” Barrymore said.
The interaction quickly went viral after the clip was shared online, with viewers praising Barrymore’s genuine reaction, and tenderly remembering that one night nearly 40 years ago.
“I can’t get past the 90s being vintage,” a reader said. “I remember watching that Oscar’s and seeing her walk the red carpet with Corey Feldman!”
Even Betsey Johnson itself was moved by the tribute.
“Nothing beats the history of a girl and her Betsey Johnson dress,” the official Instagram account wrote.
“So sweet.” Barrymore’s fans were moved by the gesture
