Jimmy Kimmel Brutally Roasts Martha Stewart's Homeless Halloween Costume, 'Your Assistant Hates You'
The late-night host stopped at nothing to poke fun at Martha Stewart's controversial costume choice, dressing up as a homeless person despite being one of the richest celebrities.
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Add BollywoodShaadis on GoogleMartha Stewart's Halloween costume choice failed miserably after her followers started criticizing her for being 'insensitive' to a very serious reality of many citizens' lives: homelessness. While Stewart took down the post hours after sharing it on social media, the damage was done.
Late-night host Jimmy Kimmel has also joined the growing list of people poking fun at Stewart's controversial look, taking sharp digs at the lifestyle mogul whose net worth puts her among the industry's elites.
Jimmy Kimmel mocks Martha Stewart's 'ridiculous' Halloween costume
The Jimmy Kimmel Live! host didn't hold back during his Monday monologue, taking several sharp digs at Martha Stewart dressing up as a homeless person despite immense wealth. Kimmel began his monologue by admitting that he enjoys watching "rich famous people get hammered for their costumes the day after."
Stewart, an 85-year-old businesswoman, decided to dress up as a person experiencing homelessness, complete with distressed clothing, dirt smeared across her face, and a cardboard sign that read, “I am hungry. Help me!!”
Reacting to the since-deleted Instagram photograph, Kimmel quipped, “That's how bad Trump's economy is. Even Martha Stewart is homeless.” The comedian wasn't done yet. He went on to question how Stewart's team had allowed the photograph to be taken and shared in the first place. He joked:
"Now how does this happen? How does this woman wind up in that costume being photographed and posted? This is how you know your assistant hates you."
While intended as a joke, Kimmel's jibe has raised eyebrows after a former colleague hinted at Stewart losing her edge, claiming that "it feels like the twinkle has disappeared," according to a new Daily Mail report. The insider also suggested that people have noticed the change in her attitude. There is no warmth or humor, which was once an innate part of Martha's larger-than-life personality.
Following the backlash, Stewart initially defended her Halloween look in a statement to Page Six. She explained that the costume was intended to bring attention to homelessness, which she described as one of America's most serious ongoing challenges. She said:
"I am distressed that my Halloween costume yesterday, which was intended to bring more awareness to the very serious subject of homelessness, has offended people, which was never my intention."
The entrepreneur also highlighted her active involvement in charities supporting the homeless and insisted that she is committed to making a difference in society. However, it looks like Jimmy Kimmel wasn't convinced by the explanation. Calling it “strike two” in the Halloween controversy, he offered Stewart some advice, acknowledging that her explanation had not gone far enough. Kimmel said:
"Here's a good general rule of thumb, OK? Don't use your Halloween costume to raise awareness of anything other than Halloween, especially when you complete the look with a boyfriend sweater from The Row."
Martha Stewart's apology sparks fresh backlash across social media
Stewart seems to be less bothered, if at all, by the ongoing criticism about her costume choice. After her initial response was criticized, Stewart issued a second statement on Instagram, acknowledging that her explanation had not gone far enough. She wrote:
"It's hard to admit when you've really screwed up. My earlier statement didn't go far enough. I know many people are suffering economically. Wearing a costume like I did was insensitive and not funny. I am very sorry."
Despite addressing the controversy, Stewart continued posting on social media. One of her latest uploads, featuring complimentary pastries from the newly opened Altbau bakery in Brooklyn, New York, attracted another round of criticism.
Some of her followers questioned the timing of the post, with one suggesting she should give the bread to hungry people. Another said, “Her PR team must be livid at what is going on." It's no news that Stewart has been under immense online scrutiny for the Halloween costume controversy. Now, Kimmel’s monologue has added a new layer of late-night humor to the discussion.
How do you feel about Jimmy Kimmel's dig at Martha Stewart's Halloween 2026 look?
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