The current article reflects on the topic of intergenerational conflict between those Cubans who lived closer to the beginning of the Castro-led Revolution of 1959, and those who were born closer to the beginning of the 1990s, during the fall of the Soviet Union, now referred to as the Special Period in the Time of Peace. In the documentary Lázaro and the Shark: Cuba under the Surface (2022), Cuban exile director William Sabourin O'Reilly showcases this national conflict. Through the screen, O’Reilly highlights the beauty of the Afro-influence combined with the intimate and lively rivalry between Santiago’s local Conga groups in a country riddled by harsh conditions to dive deeper into the ever-growing intergenerational conflict. Within this current conflict, Cuba’s generations are separated into Fidelists and Oppositionalists; in opposition to the Pragmatist and the Disengaged generation (Krull and Kobayashi). With recent restrictive legislation for Cuban filmmakers, the director’s ability to make a controversial documentary of this nature is only possible from outside of Cuba as an exile.