This study explores the normalisation of ―Yahoo Yahoo‖ (as cybercrime is called in popular parlance among Nigerian youth) and traces its representation in music, on social media, and within operatives‘ communities. Applying a mixed-method approach that incorporates content analysis of Nigeria‘s top songs between 2017 and 2024 and sentiment analysis of 8,000 tweets, the study illuminates how dishonorable conduct is beginning to be seen more as aspirational rather than criminal. Celebrities such as ShallisPopi and Naira Marley, were discovered to have played prominent roles in the spreading of Yahoo-related slang and glorifying narratives that fetishize instant wealth, street ―rep‖ and material opulence. This study relates the perception of Nigerians to the socio-economic issues of high rates of unemployment among the youth, poverty, and the absence of digital opportunities. It also identifies that there is a gap in the current body of literature, especially the absence of factual study on the impact of pop culture/social media on the attitude of the youth towards cyber crimes. Discovery states that Yahoo Yahoo is more than just an issue that requires criminalization but is an indicator or a result of systemic inequality/disappointment. The study indicates that to address this issue, measures beyond enforcement are needed; there is a need for ethical orientation, digital literacy, proper depiction by the media, as well as empowerment of the youths to provide viable alternatives for cybercrime.