An unprecedented number of films directed and often written and produced by African Americans offering coupling conventions or the marriage plot as a trope began emerging at the close of the twentieth century and have continued with strong popularity into the twenty-first. The initial emergence of these films came on the tail of vicious debates and public rhetoric about dysfunctional African American families. As a means of talking back, or perhaps even conforming to social policy, black film embraced marriage plots. Most of the films, however, end with a wedding, which prevents audiences the opportunity to imagine a status—marriage—that the media, politicians, social scientists, and popular culture propose is antithetical to blackness. Ending with the wedding begs the question: What happens after “I do?” Malcolm Lee’s The Best Man (1999) and its long-awaited sequel The Best Man Holiday (2013) offer spectators a fairytale story of black success and black love after “I do.” Because Lee’s film enterprise imagines black marriage after the wedding, it is a useful case study for how narratives of blackness in the realm of popular culture talk back to popular public sphere narratives of unmarriageable black women, criminalized black men, and wayward black children. Ultimately, The Best Man Holiday is a what I call a “black-black” film that, through its depiction of black marriage and black children, enables blackness to function as an analytic that gives meaning to black joy in twenty-first century popular culture.