The "guilt" associated with enjoying Da Vinci's "Conquistador" largely stems from viewing its quintessentially 1989 characteristics through a modern lens. The most significant factor is the song's lyrical content. It serves as an unapologetic and romanticised ode to Portugal's colonial history, proudly listing former territories like Brazil, Angola, and Mozambique. In today's more historically conscious era, the celebratory theme of being a "conqueror" can feel jarring and politically tone-deaf, creating a sense of thematic awkwardness for the listener.
Beyond the lyrics, the song's musical production contributes to the "guilty" feeling. The once-futuristic synthesizers and digital drum machines now sound wonderfully cheesy, firmly dating the track as a product of its time. The performance also leans into beloved but often-mocked musical tropes, such as a dramatic key change designed to heighten the emotional climax, which adds another layer of delightful retro cringe. Finally, its lacklustre 16th-place finish at the contest gives it an underdog status. Championing a song that was commercially and critically overlooked by Europe adds to the feeling that it is a special, if slightly flawed, personal favourite.