Los Angeles — In the wake of pop sensation Billie Eilish's pointed remarks on immigration and indigenous land rights during her acceptance speech at the 68th Annual Grammy Awards, business magnate and 'Shark Tank' star Kevin O'Leary has issued a blunt advisory to celebrities: stick to entertaining and avoid political commentary. O'Leary, chairman of O'Leary Ventures, made his comments during an appearance on Fox News' 'America Reports' on Tuesday, just days after the Grammys ceremony held on Sunday, February 1, 2026, at Crypto.com Arena in Los Angeles.
Eilish, 24, won the Grammy for Song of the Year for her track, which she co-wrote and performed. As she accepted the award, the singer declared, 'no one is illegal on stolen land,' a statement that appeared to critique U.S. border enforcement policies and the role of Immigration and Customs Enforcement, or ICE. The comment drew immediate attention, sparking discussions about the intersection of celebrity activism and entertainment awards shows.
O'Leary, known for his no-nonsense investment advice on television, didn't hold back in his assessment of Eilish's decision to use the platform for political expression. 'Half the people in politics that you piss off won't buy your music anymore,' he told host Sandra Smith on 'America Reports.' He added, 'Don't be stupid about it, but hey, they don't listen,' suggesting that celebrities like Eilish often ignore the potential backlash from alienating fans.
The investor went further, framing such moments as a fundamental misstep in a celebrity's career trajectory. 'It's the first lesson 101 for celebrity: As you rise up, whether you're a film star, a music star [or] whatever, shut your mouth and just entertain,' O'Leary said. He speculated that Eilish's agents were 'going out of their minds' over the speech, implying internal panic within her management team about the commercial risks involved.
Eilish's remarks were not isolated; the Grammys have long served as a stage for artists to address social and political issues. For instance, during the ceremony, other performers and winners voiced criticisms of the Trump administration's immigration policies. Eilish herself has previously spoken out on related topics, including in a separate award speech where she said protesters are being 'assaulted and murdered,' according to reports from the event.
The response from indigenous communities added another layer to the conversation. The Tongva Tribe, recognized as the First People of the greater Los Angeles basin, issued a statement to Fox News Digital appreciating Eilish's nod to historical injustices. 'We appreciate the opportunity to provide clarity regarding the recent comments made by Billie Eilish,' the tribe said. They noted that Eilish's home is located on their ancestral land and that she has not contacted them directly about her property.
While valuing the visibility brought by the singer's comments, the Tongva emphasized the importance of specificity in such discussions. 'As the First People of the greater Los Angeles basin, we do understand that her home is situated in our ancestral land. Eilish has not contacted our tribe directly regarding her property, we do value the instance when Public Figures provide visibility to the true history of this country,' the statement read. The tribe continued, expressing hope for future engagements: 'We have reached out to her team to express our appreciation for her comments. It is our hope that in future discussions, the tribe can explicitly be referenced to ensure the public understands that the greater Los Angeles basin remains Gabrieleno Tongva territory.'
Fox News Digital reported that they had reached out to Eilish's representatives for comment but received no response at the time of publication. This lack of direct reply from the singer's camp leaves open questions about how her team views the fallout from the speech.
O'Leary's critique echoes sentiments expressed by other public figures in the entertainment industry. Comedian Ricky Gervais, for example, has mocked Grammy winners for making political speeches, reportedly saying they are 'still not listening' to advice against it. Gervais's comments, though not directly tied to this year's event, highlight a recurring debate about the appropriateness of activism at award shows.
The Grammys, organized by the Recording Academy, have a history of blending music celebration with social commentary. Past ceremonies have featured speeches on topics ranging from racial justice to climate change, often eliciting both praise and criticism. Eilish's win for Song of the Year underscores her rising influence; the category recognizes outstanding songwriting, and her victory places her among elite songwriters like Taylor Swift and Kendrick Lamar, who were also nominees this year.
From a business perspective, O'Leary's warning carries weight given his experience in entertainment investments. As chairman of O'Leary Ventures, he has invested in numerous media and consumer brands, often emphasizing the importance of broad appeal. His appearance on 'America Reports' was part of a broader discussion on celebrity culture and its economic implications, with co-hosts probing how such statements might affect album sales and touring revenue.
Eilish, who hails from Los Angeles, has built a career on authenticity, blending introspective lyrics with bold public stances. Her 2026 Grammy win marks another milestone following previous accolades, including multiple wins at the 2021 and 2024 ceremonies. However, the 'stolen land' comment specifically references the complex history of indigenous displacement in California, where the Tongva people were removed from their lands during Spanish and American colonization.
The Tongva's response suggests a nuanced appreciation rather than outright endorsement. By reaching out to Eilish's team, they aim to foster dialogue, potentially leading to more informed advocacy. Tribal leaders have long sought greater recognition in public discourse, and Eilish's platform could amplify their voice if collaborations ensue.
Looking ahead, O'Leary's advice may resonate with emerging artists navigating the pressures of fame. As award seasons continue, including upcoming events like the Oscars in March 2026, the tension between entertainment and activism is likely to persist. For Eilish, whose next album is anticipated later this year, the speech could either galvanize her fanbase or, as O'Leary predicts, lead to divided support.
Ultimately, the incident at the Grammys illustrates the high stakes for celebrities in an era of polarized opinions. While Eilish's words sparked conversation, they also invited scrutiny from figures like O'Leary, reminding the industry that every stage moment carries commercial consequences. As the dust settles, all eyes remain on how Eilish and her team respond to the indigenous community's outreach and the broader cultural debate.