Dolly Parton’s playful challenge with Conan O’Brien leads to wild TV moment no one saw coming
Dolly Parton couldn't stop flirting with the handsome host when she appeared on 'Late Night With Conan O'Brien' in 2001. Parton practically fulfilled the comedian's fantasy by accepting his risqué challenge on live TV. O'Brien couldn't contain his excitement and was all over the 'Jolene' hitmaker from the word go. "Hello there, let me help you," he said while trying to keep his hands off her. "You want to help me with my double-breasted suit," Parton quipped as she adjusted her mic. "You look fantastic," the comedian continued, maintaining flirtatious eye contact. Their banter carried on till Parton narrated a strip dare she performed at the request of her friends, "I dare you to take off all your clothes right now." O'Brien threw an impromptu challenge at the country star at that moment.
The Grammy winner hesitated, but O'Brien didn't budge. "I mentioned up top, this is February sweeps. I think we have people's attention now. I double dog dare you to take off all your clothes. Come on! Come on! You have to." Parton turned nervous and started shaking her legs; she tried to fend off the awkward situation but to no avail. "I will help you take it off," the late-night host further encouraged. The 'I Will Always Love You' hitmaker then reluctantly stood up, and O'Brien helped take off her outfit. He then proceeded to unzip her leather pants, and the screen went blank with a hilarious statutory warning from the network. 'We are experiencing technical difficulties. Please standby.'
When it eventually came back on, the crowd was roaring with laughter. Parton could be seen adjusting her top; however, her jacket lay on top of O'Brien's shoulder. The comedian's hair looked disheveled as if from a frisky activity, and his tie was also out of place. The scene looked like complete chaos with the host mockingly burying his head in shame, "What's good for me? What's it good for you? I am in the tablo now," Parton teased a bewildered O'Brien, referring to making it to the headlines with her raunchy act. The viral video has since garnered over 3 million views on YouTube, and fans loved watching Parton's free-spirited nature, "the only woman who could make trash sound so endearing. I love how honest and good-spirited she is," a viewer gushed.
"Conan's facial expression in the thumbnail is priceless!" a fan pointed out. One netizen said, "The technical difficulties scene transition was funny as hell," a netizen joked. "First 5 seconds and she refers to her own "double-breasted suit " She's such a firecracker; what a lovely woman," another fan chimed. During the interview, Parton casually recalled that she had accepted a challenge to run across Welsh singer Tom Jones' yard naked. As per Fandomwire, she recounted the incident in her autobiography 'Dolly: My Life and Other Unfinished Business.' "I felt the cool grass of Tom Jones’s yard on my bare feet. Of course, that was a perfect complement to my bare ass parading around in the swankiest part of LA for all to see," she wrote about her controversial escapade without any remorse.