Taylor Swift’s Missing Trophies: Pop Superstar Targets 2027 Grammys to Break Her Track-Category Curse

Taylor Swift remains the undisputed queen of the Grammy Awards main stage, but her trophy cabinet is missing two of the biggest honors in music. The pop superstar has racked up a record-breaking four Album of the Year victories, yet she has never walked away with Record of the Year or Song of the Year. That historical drought sets up a fascinating strategic battlefield for future award cycles. Reports highlight that Swift currently boasts three distinct Billboard Hot 100 No. 1 singles eligible for the 2027 Grammy Awards eligibility window, forcing her team to make some calculated submission choices. ## Has Taylor Swift ever won Song of the Year at the Grammys? Despite dozens of nominations throughout her career, the Recording Academy has repeatedly bypassed Swift in the top two singles categories. Music commentators often point out the bizarre duality of her Grammy record: she is simultaneously one of the most celebrated artists in Academy history and one of its most frequently overlooked nominees in the song-specific races. Song of the Year specifically recognizes the craft of songwriting, an honor that holds immense personal weight for an artist who has built her entire legacy on her penmanship. While her full-length albums consistently capture the Academy's top prize, her individual singles have repeatedly missed out to competing pop hits. ## What hits could Taylor Swift submit for the 2027 Grammys? Having three eligible chart-topping tracks in a single eligibility cycle creates a classic voting predicament. Pushing multiple songs in the same category can backfire by splitting votes among Academy members, ultimately opening the door for rival artists to swoop in and take the prize. Industry insiders note that Swift will likely need to select one main track to champion for Song of the Year and Record of the Year to avoid diluting her support. Concentrating her campaign power behind a single standout hit could provide her best opportunity yet to finally break her track-category curse. With the 2027 cycle still on the horizon, fans and critics alike will be watching closely to see how the pop titan navigates her submissions. Whether she focuses her energy on one definitive single or lets the voters decide, the pressure is officially on to capture the major trophies that have eluded her for decades.