Pop superstar Taylor Swift made a highly anticipated return to The Late Show With Stephen Colbert on Wednesday, December 10, marking her first in-person appearance on the show since 2021. The visit was highlighted by a delightful backstage TikTok video with host Stephen Colbert, where the duo paid homage to Swift's 2008 Fearless album cut, "Hey Stephen."

The charming video begins with a close-up of Swift, sporting a red lip and a fuzzy winter jacket, swaying to the familiar humming intro of "Hey Stephen." As the camera pulls back, it reveals Stephen Colbert beside her, who comically lip-syncs the song's first word, "Yeah." Swift then breaks into a wide, goofy smile, waving at the late-night host and mouthing, "Hey, Stephen!" Despite never being released as a single, the jangly country-pop track achieved a notable peak of No. 94 on the Billboard Hot 100 during the week Fearless debuted.

During a previous virtual appearance on The Late Show in 2021, Colbert playfully inquired if he was the inspiration behind the unrequited-love song. Swift humorously brushed off the notion, quipping, "Don’t flatter yourself," and joked that the song was actually about author Stephen King, praising his works like The Dark Tower series, The Shining, and The Stand. However, Swift had previously confirmed that the titular love interest was indeed Stephen Barker Liles from the country duo Love and Theft, who opened for her in 2008, a detail she explicitly provided in the Fearless liner notes.

Beyond the viral TikTok moment, Swift faced a challenging task during her interview with Colbert: naming her top five songs from her extensive catalog. This demanding quiz placed Swift in the esteemed company of music legends like Dolly Parton, Elton John, Paul Simon, and Bruce Springsteen, all Rock and Roll Hall of Fame inductees, a recognition many believe is only a matter of time for Swift.

Swift openly struggled with the request, telling Colbert, "This is so much pressure." She requested more time to compile a definitive list, explaining, "Because I don’t have enough, see. I think I require a little bit of time to like, appreciate my work in a way… and it’s constantly changing, right. It’s a little too soon." Despite the difficulty, she managed to select her first choice: the acclaimed 10-minute version of "All Too Well," released as part of her re-recorded Red (Taylor’s Version) in November 2021. She also mentioned, "I’m really obsessed with The Life of a Showgirl right now, the whole album," before also selecting Mirrorball from her 2020 Folklore album, admitting she "can’t really do any of the others" at that moment.

Colbert, with his characteristic sharp wit, granted Swift a specific deadline, remarking, "You’ve got all the time you need between now and May." This timeframe is significant, as Colbert is slated to conclude his tenure on CBS' airwaves after May. The Late Show with Stephen Colbert featuring Taylor Swift aired Wednesday night at 11:35 p.m. ET on CBS and was also available for streaming on Paramount+.