‘Plastered on All the Cocktail Tables’: Jennifer Hudson Spills on How Her Oscar-Winning Night Turned into a Complete Disaster Within Hours

Jennifer Hudson has a rather “surreal” moment that she recalls from the night she won her first Oscar in 2007. 

At the Academy Awards in 2007, Hudson won Best Supporting Actress for her film debut as Effie White in the 2006 film “Dreamgirls.” What should’ve been — and probably was — a cloud 9 moment for the daytime talk show host turned sour by the end of the night.

Jennifer Hudson opens up about the time she got worst dressed during her Oscar-winning night in 2007. (Photo by Leon Bennett/Getty Images for the Critics Choice Association)

The EGOT winner sat with Andy Cohen on his  “What What Happens Live” show on Oct. 13, where she opened up about the gown that stole her spotlight instead.

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Cohen asked Hudson, “To this day, what’s the most surreal moment you remember from the night you won your Oscar?”

Taking a moment to pause and think, Hudson responded, “Being worst dressed.”

Stunned by the response, Cohen said, “Really! Were you!?”

“No, no, no,” she said. “Seriously. After I won the Oscar, we went to the after parties and plastered on all the cocktail tables [was] ‘Jennifer Hudson Worst Dressed.’”

Actress Laverne Cox, who was also a guest on Cohen’s show, asked with shock, “They had it on their tables?”

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Was Jennifer Hudson really “worst dressed” the night she won her Oscar in 2007? WWHL

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Hudson turned to her and said, “Yes girl. On the cover of different things.”

Cox, who needed more clarity, asked, “What!? The night of?”

The “Respect” star said, “They don’t care. Yes.” 

That night, Hudson wore a brown Oscar de la Renta gown along with a gold metallic bolero. Some say the bolero, which is a cropped jacket, is what made the look a disaster.

Even Hudson wasn’t a fan of her attire, but the late stylist and former Vogue creative director André Leon Talley reportedly insisted. According to Glam.com she removed the bolero later on that night which you can see when she walks upstage to accept her award.

However, it appears she didn’t let the incident keep her down. “But it’s OK I set that Oscar and I put it on top of it,” Hudson stated.

Fans on The Neighborhood Talk responded to the clip in the comments, with some sharing the same sentiment about her dress.

One person said, “That’s crazy, same night though? Somebody wanted to tear her down during her big moment, that’s way too intentional lol.”

Another wrote, “Andre Leon Tally betrayed you with that dress doll we all saw it but we still rooted for you.”

Apparently, people still aren’t a big fan of her fashion choices today, especially on her eponymous show. 

One person said, “And this still remains. I love Jen but the stylist be playing on that daytime show.”

A second wrote, “Not surprised!!! Her style is so dated on her show too…she deserves better.”

Hudson admitted that while the recognition felt like a dream come true, the backlash over her brown metallic bolero, a look chosen by her then stylist, quickly dimmed the glow of the night. Looking back, she laughed off the fashion misstep, saying it taught her an early lesson about trusting her instincts and owning her image.

“It was my first time at the Oscars,” she said, “so I just went with it.” Now, years later, she can joke about the moment that once stung, reminding fans that even on Hollywood’s biggest stage, confidence outshines any red carpet critique.

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