Imagine your favorite pop superstar and a late-night legend teaming up for a TikTok video that’s equal parts adorable and nostalgic. That’s exactly what happened when Taylor Swift and Stephen Colbert reunited backstage at The Late Show—and it’s as charming as it sounds. But here’s where it gets even better: their soundtrack? None other than Swift’s 2008 gem, ‘Hey Stephen,’ a song that’s never been released as a single but still holds a special place in fans’ hearts.
The video kicks off with Swift, rocking a bold red lip and a cozy winter jacket, grooving to the humming intro of the track. As the camera pulls back, we spot Colbert himself, lip-syncing the opening ‘Yeah’ with perfect comedic timing. Swift, who’d been playing it cool, breaks into a goofy grin, waves at Colbert, and mouths, ‘Hey, Stephen!’—a moment so wholesome it’s hard not to smile along.
And this is the part most people miss: while ‘Hey Stephen’ never climbed the charts as a single, it did sneak onto the Billboard Hot 100, peaking at No. 94 when the Fearless album debuted. But who’s the real ‘Stephen’ behind the song? That’s where things get controversial. During Swift’s 2021 virtual appearance on The Late Show, Colbert jokingly asked if he was the inspiration. Swift playfully shut him down, quipping, ‘Don’t flatter yourself,’ and teasing that it was actually about author Stephen King. ‘He’s amazing,’ she gushed, citing The Dark Tower series and The Shining as life-changing works.
However, Swift has since confirmed the song was inspired by Stephen Barker Liles of the country duo Love and Theft, who opened for her in 2008. She even spelled out his group’s name in the Fearless liner notes as proof. So, was Colbert ever really in the running? Probably not—but it’s fun to imagine.
Swift’s return to The Late Show on Wednesday night (Dec. 10) marks her first appearance since that 2021 segment. Catch her at 11:35 p.m. ET on CBS or streaming on Paramount+. And here’s a thought to leave you with: If ‘Hey Stephen’ isn’t about Colbert or King, who else could it be about? Let us know your theories in the comments—this is one mystery Swifties might never fully solve!
