"Swing, Swing" was written by Nick Wheeler and Tyson Ritter. According to Ritter, the song was written in his grandparents' cabin in his hometown of Stillwater in Oklahoma when he came up with the chorus one weekend morning. "My ex-girlfriend and I had a rough relationship, and that was written when it sucked real bad," Ritter explained, "I liked this other chick, so that's what the second verse is about, moving on to a hotter chick - no I'm just kidding. Moving on to another girl... or just moving on." 
The song was also one of the last to be written and recorded for the duo's self titled debut album "It was over and done with a year ago," Ritter said of the misery-inducing relationship that also inspired many other tear-jerking pop songs, such as "My Paper Heart" and "Don't Leave Me." "But I got a great record out of it... as far as lyrics. I didn't have to think too hard." 
The song received generally positive reviews from music critics. Rockfeedback, who rated the track 3 out of 5 stars, reviewed the song as "Very polished, insanely catchy, and heart-on-sleeve this record is. Dramatically expressive lyrics ('Did you think that I would cry, on the phone...?', 'My heart is crushed by a former love!'), ultra-glossy production and a ridiculously infectious chorus: you wouldn't bet against them." Contactmusic.com said "The melody is appealing and its pop punk sounds like something from Simple Plan or Blink 182. The lyrics are slightly baffling with 'swing, swing, swing from the tangles of' - a classic example." 
MusicOMH regarded "Swing, Swing" as "top form" and commented with "These small-town American, fun rockers are hard to dislike. Swing Swing swings along pleasantly enough, developing from an organ intro to a good-natured, old-style rock out that does just what you expect it to. Rock, that is",  while CityLife praised the track as "imaginative" and that "The use of a church organ gives way to a totally catchy - if formulaic - college rock anthem. Vocals are typically American high-pitched angst, while the simple "Swing-Swing" chorus should guarantee favourable radio play on both sides of the Atlantic." 
The music video for "Swing, Swing" was directed by Marcos Siega and shot in December 2002 in Los Angeles and was released on January 7, 2003. It involves the band performing the song in a small trailer park while scenes of a young couple going through their relationship are overlapped through the video - eventually ending with them breaking up.