Songfacts®:

• Jake Owen's first single on Big Loud Records is a nostalgic upbeat track that finds him reminiscing about the days he and a girl were teenagers listening to pop tunes and experiencing young love. Owen spent over a decade at RCA Nashville, releasing five studio albums before signing with Big Loud Records in November 2017.
• Written by David Ray, Jody Stevens and Craig Wiseman, the song opens with the hook from John Mellencamp (then John Cougar)'s classic rock number "Jack & Diane" and samples the 1982 hit tune throughout the track.
• "I Was Jack (You Were Diane)" uses Cougar's famous song to look back on a past relationship between "two American kids, just like them."
  
  "I never release a song without the intention of stepping up to the plate and knocking it out of the park," said Owen. "When I first heard 'I Was Jack (You Were Diane),' I thought, 'How can I do this and re-create what is already a classic song?' But the more I listened to it, the more I saw my own life growing up."
  
  "The original 'Jack & Diane' was about 'two American kids growing up in the heartland' and that image is exactly what so many country songs are based on. Plus, the most important thing to me and my team is that we sent the song to Mellencamp and he digs the track. Getting his stamp of approval sealed the deal for me that this song should be our debut single."
• The song's 9-minute music video was directed by Justin Clough. It features a small-town high school romance between Jake Etheridge, of the TV show Nashville and Travelers actress (and his real-life girlfriend) Mackenzie Porter. Jake Owen shows up as the waiter that comes to the table to ask the pair what they'd like to order.
• The visual uses local actors and extras from the location where it was filmed to achieve authenticity. "Which is funny, because the part of the video where they were playing baseball, that was actually happening that night," Owen recalled at the video's viewing party. "There were two teams playing baseball, and one of the teams got mercy-ruled - they got beat so bad. The team that acts like they won the championship [in the video] is actually the one that got the s--t kicked out of them in real life, 30 minutes previously. So at least they got to celebrate that night, thanks to us!"
• It's ironic the song is one of the most successful of Jake Owen's career. He used to play "Jack & Diane" multiple times at college and its one of three tunes the singer vowed never to perform again once he'd made it. The other two that he overly played were "The Joker" and "Sweet Home Alabama."