Anna Nicole Smith’s appearance on Late Night with Conan O’Brien in the early 2000s remains one of the most memorable—and awkward—moments in late-night television history. Known for her larger-than-life personality, Smith was at the height of her fame, having recently married the elderly oil tycoon J. Howard Marshall. When she sat down with Conan, the interaction quickly took a humorous and unexpectedly uncomfortable turn.

As Conan tried to engage her in a playful conversation about her life and career, Anna Nicole seemed somewhat disoriented and confused. At one point, when Conan asked her a straightforward question, she gave a response that left the audience—and Conan himself—stunned. She didn’t seem to follow the conversation, giving responses that were out of place, causing the host to look genuinely puzzled. The more he tried to steer the conversation back on track, the more awkward the situation became.

Despite the uncomfortable moment, Anna Nicole remained gracious, laughing off the incident, but it only added fuel to the media frenzy around her. People speculated whether her behavior was a result of nerves, a scripted bit, or something else entirely. For viewers, it was both cringe-worthy and captivating, making it one of the most talked-about late-night moments of its time.

In the end, the incident became part of Anna Nicole’s larger-than-life persona—a blend of vulnerability, charisma, and unpredictability. Whether intentionally or not, she cemented her place in pop culture, reminding audiences that sometimes, reality is far stranger (and more entertaining) than anything scripted TV could produce.