"Checkmate" is a collaborative song by Jelly Roll and Struggle Jennings. The lyrics depict their struggles, triumphs, and determination in the face of adversity. The song begins with Jelly Roll acknowledging the need to approach life differently when emotions and personal stakes are involved. He realizes that talking negatively and stirring up problems won't solve anything but rather exacerbate the issues. They both talk about their experiences and successes, having just returned from a tour and stacking up finances. They compare themselves to King Kong, emphasizing their dominance and unwillingness to engage in pointless arguments. Jelly Roll claims that he deserves recognition for enduring hardships, comparing himself to a soldier with a purple heart. He explains that he embraced the moniker "bad apple" because he was constantly belittled and called names, yet he kept coming back for more. The artists also address the presence of deceitful individuals, symbolized by snakes in the grass. They discuss the repercussions of getting involved with people who are not genuine, as it almost caused them to lose someone valuable (possibly a loved one or partner). The chorus, "Loose screw, tight circle, Eradicate, dead weight, My move, your move, My move, checkmate," signifies their determination to eliminate negative influences from their lives and make calculated, strategic moves to ensure their success. They acknowledge that they won't lose or fail easily because they have the strength and greatness within them. In the second verse, Struggle Jennings reflects on avoiding a destructive outcome by leaving before things can crash and burn. He refers to himself as calm in the face of death, and contrasts this with deceitful individuals who twist the truth. Struggle Jennings declares that while others engage in petty arguments and gossip, he is focused and unbothered, maintaining his intelligence and unpredictability like a "loose cannon." He advises others to stay out of his business and asserts his superiority. The artists also touch on the concept of redemption, acknowledging past mistakes and seeking forgiveness. They express their dissatisfaction with those who judge without knowing the full story, emphasizing the importance of thinking before making assumptions. The song concludes with a reference to the game of chess, as they plan their next move strategically, vowing to make it their best move. They proclaim that their previous choices were leading up to this moment and declare victory over their detractors. Overall, "Checkmate" is a powerful song that speaks to resilience, perseverance, and personal growth in the face of adversity. It emphasizes the need to cut ties with toxic influences, make well-thought-out moves, and strive for personal excellence.