
Taylor Swift Struggles to Name Her Five Favorite “TayTay” Songs During Playful Visit to ‘The Late Show’
Taylor Swift may be one of the most prolific songwriters of her generation, but even she finds it nearly impossible to narrow down her own catalog. During her visit to The Late Show With Stephen Colbert on Wednesday, Dec. 10, the pop superstar was confronted with a deceptively simple challenge from the outgoing host: name her top five “TayTay” songs. It quickly became clear that the task was anything but simple.
Colbert’s request places Swift in distinguished company. Dolly Parton, Elton John, Paul Simon, and Bruce Springsteen — all Rock & Roll Hall of Famers — have previously taken part in the same on-air musical ranking exercise. Swift, whose own induction into the Hall feels like an eventual certainty, gamely attempted the list but immediately felt the pressure.
“This is so much pressure,” she admitted with a laugh, noticing that Colbert had already begun jotting down her answers. The singer went on to explain that she’d need more time before committing to a definitive ranking of her work. “I think I require a little bit of time to appreciate my work in a way… and it’s constantly changing. It’s a little too soon.”
Even so, Swift did manage to give Colbert at least one firm answer: her top pick is the acclaimed 10-minute version of “All Too Well,” released in 2021 as part of Red (Taylor’s Version). She added that she’s currently “obsessed” with her new album The Life of a Showgirl, which recently debuted to strong fan enthusiasm, and also named “Mirrorball” from 2020’s Folklore as a personal favorite. Beyond that, however, she hesitated. “I can’t really do any of the others,” she confessed, requesting time to revise her list in the future. “Maybe we could do an update at some point.”
Colbert, known for his quick-fire delivery, couldn’t resist a joke. “You’ve got all the time you need between now and May,” he quipped, referencing the date his long-running late-night show will officially conclude on CBS.
Swift’s challenge wasn’t the only moment capturing fans’ attention. For her first visit to The Late Show since 2021, she filmed a charming TikTok backstage with Colbert. The video begins with Swift, wrapped in a fuzzy winter coat, bopping along to the humming intro of her 2008 Fearless deep cut “Hey Stephen.” When the camera pans out, Colbert is revealed beside her, lip-syncing the song’s first word: “Yeah.” Swift drops her straight-faced pose, flashes a wide grin, and waves at the host while mouthing, “Hey, Stephen!”
The playful moment quickly spread across social platforms, adding another viral highlight to Swift’s already headline-heavy week.
Fans can watch her full conversation with Colbert — including the partial top-five reveal and the good-natured back-and-forth — on The Late Show’s official channels.
