Songfacts®:

• Taylor Swift explained this song to Philadelphia Magazine: "This is a guy I had a crush on. I wrote about all these reasons he should be with me instead of other girls. [laughs] 'Hey Stephen/I could give you 50 reasons/Why I should be the one you choose/All those other girls are beautiful/But would they write a song for you?' This guy has absolutely no idea I had a crush on him. It's gonna be kind of interesting when he finds out."
• Country singer Martina McBride's children lend finger snaps at the end of this upright-bass-propelled groove. Taylor Swift explained to That's Country how she got the kids involved: "We were recording at John McBride's (Martina McBride's husband's) studio and he was like, 'My kids are dying to meet you. Do you think that you could say hi to them?' I said, 'Sure, have them come and hang out while we're recording.' So his daughters and their friends from school – there were about ten of them there – they all came into the studio when we were recording "Hey Stephen" and they loved it. They were singing along with it by the end of it."
• It appears that the subject of this song is singer Stephen Barker Liles of the country music group Love and Theft. Liles first met Swift backstage at an event in 2007. Shortly before being signed, the band was picked to be an opening act for Swift on her 2008 tour. Evidently the vocalist made an impression on her and if he didn't realize it then, the penny probably dropped when Liles got a call from Swift hinting that he was featured on Fearless. He told People Magazine: "It's totally flattering to have somebody write a song like that for you." While Swift won't officially confirm the subject of her song, the words "Love and Theft" are spelled out in code in the song's lyric sheet.
• Taylor Swift redid the song in 2021 for Fearless (Taylor's Version), her re-recording of her 2008 album. When she appeared on The Late Show with Stephen Colbert to discuss the record, the late night personality questioned whether "Hey Stephen" was written about him, which Swift denied. "It's just the power of music," she said, adding, "Don't flatter yourself."
  
  Swift continued the sketch holding up a mood board covered in pictures of Colbert's face that she claimed originally inspired the song, Finally, she jokingly revealed that she'd actually penned the tune about novelist Stephen King.