At the 2025 Academy Awards, Conan O'Brien delivered one of the most blistering monologues in recent memory, with one clear target—Meghan Markle's Netflix series With Love. The audience erupted with laughter as O'Brien skewered what he called the delusional self-importance behind Meghan’s latest project.
Intended as a heartfelt documentary about her and Prince Harry’s philanthropic work and struggles with the British monarchy, the series ended up being perceived as a transparent attempt to reinforce Meghan’s image as a major entertainment figure. O'Brien didn’t mince words, highlighting how an evening meant to celebrate cinematic excellence had taken a detour into publicly dissecting Meghan’s ongoing quest for relevance in Hollywood.
Rather than inspiring viewers with stories of resilience and compassion, the series was widely criticized for being self-indulgent and repetitive. Critics and viewers alike panned it as unoriginal and lacking in emotional depth. Even some of Meghan's most ardent supporters found it difficult to defend the show's uninspired content. Online, social media lit up with scathing commentary, many users expressing fatigue over the recycled narrative. One of O'Brien’s sharpest jabs summed it up: “I watched With Love, and now I truly know what suffering looks like—not Meghan’s, but ours, as we sat through it.” The line triggered roaring laughter, signaling that O'Brien had struck a cultural nerve.
Hollywood, once eager to embrace Meghan and Harry’s brand, appears to be retreating. With Love was merely the latest in a series of projects that have failed to resonate with the public. From Pearl, the animated series Netflix canceled before it reached production, to this latest misfire, Meghan’s attempts to establish a foothold in Hollywood seem increasingly shaky. Streaming services and production companies are reportedly becoming more hesitant to associate with the Sussexes. Netflix had invested heavily in With Love, banking on its success, but the tepid viewership and stinging reviews painted a starkly different picture. As one Hollywood producer put it, “You can’t keep selling the same sob story and expect people to keep buying it.”
Known for his razor-sharp wit, O'Brien didn’t let up throughout his Oscars monologue. He ridiculed Meghan’s persistent efforts to cast herself as a cultural icon and even joked about the irony of an ex-royal attempting to school the world on royalty and humanitarian values. “I’ve got to hand it to Meghan,” he said, “she managed to turn a love story into her own personal myth.” The room, packed with A-listers, burst into laughter—a telling sign that even Hollywood’s elite are growing weary of the Sussex saga.
Although Meghan and Harry did not attend the Oscars, sources close to the couple claimed they were offended by O'Brien’s jokes. Still, the overwhelmingly amused public reaction said it all. The once-bright shine of the Sussex brand is beginning to tarnish. With each failed venture, it becomes increasingly apparent that Meghan’s pursuit of Hollywood stardom is, at least for now, falling short.
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