Rapper Island Boy, known online as Flyysoulja, stepped into what he likely thought would be easy territory when content creator Hoodrichkevin set up a “20 Women vs 1 Rapper” video. Instead, Fly he into a series of conversations that left him flustered, defensive, and eventually begging for a ten-minute break.
The video opens with the aftermath already in full swing, with a woman landing one of the sharpest blow of the entire session early on. After Fly pointed out that her teeth were yellow, she responded: “Okay, that’s fine. I can get them fixed. But you can’t unkiss your brother.”
Fly’s tendency to comment on appearances before even introducing himself became a recurring problem throughout the video. One participant named Sienna stopped him mid-conversation and said, “You’re supposed to be asking my name and introducing yourself.”
His attempts to redirect the conversation only dug him deeper. Rather than recovering, Fly continued making comments about women’s looks, heights, and hair colors, which each woman threw right back at him.
When Sienna got going, she did not hold back: “You’re not. You’re my height. You’re scrawny. You’re skinnier than me. You wear a size small. You made out with your brother. Everyone thinks you’re Jeffrey Epstein’s son.”
Fly’s response was to try flexing his financial status, telling her, “I have a mansion. I have a nice car.” Her reply was simple: “I’m so proud of you.”
Another woman asked him directly, “You’re famous for what? You get clowned on the internet for fun. Good job. You’re famous for getting laughed at.” When Fly insisted his status was better than hers, she fired back, “Says who?”
Not all the interactions were hostile. A woman named Mila admitted she was a genuine fan, following Fly on TikTok and Instagram. A woman named Kayla talked about her spiritual side and her interest in painting, and Fly engaged with her more calmly than most.
Still, by the end of the video, the weight of the confrontational exchanges had taken a visible toll. Fly became overwhelmed and walked away from the setup, prompting Kevin to call for a pause. Kevin later told the group, “He’s now just overwhelmed because the girls weren’t it.”
Fly spent much of his time on defense, responding to jabs about his brother, his height, his credit score, and his face tattoo, which one woman said looked like “the slime from Nickelodeon.”
