In January 1990, They Might Be Giants performed "Your Racist Friend" on *Late Night with David Letterman*, a significant moment for the band as they were transitioning into mainstream visibility. At this time, they had recently released their album *Flood* in 1990, which would become their most commercially successful record, featuring hit singles like “Istanbul (Not Constantinople)” and “Birdhouse in Your Soul.” The performance epitomized the band's unique blend of alternative rock and witty lyrics, showcasing their appeal to a broader audience. Notably, "Your Racist Friend" addresses themes of social and political responsibility, reflecting the band's penchant for thoughtful artistry. The performance on such a prominent platform like Letterman not only highlighted their engaging live presence but also helped solidify their place in the alternative music scene during the early 1990s.