Songfacts®:

• Lanco is an American country music band fronted by Brandon Lancaster. Their name is short for Lancaster & Company.
• Penned solely by Lancaster, this nostalgic song chronicles the story of two kids who fall in love. The two childhood sweethearts step away from each other for a time before finding their way back together for good.
  
  "We've all been in relationships and we've all been through those experiences where you're with someone and then you spend some time apart," Lancaster told Taste of Country. "This specific song for me, it all started out with the first few lines of the song ('They said I was nothing but a troublemaker. Never up to no good. You were the perfect all American girl. Wouldn't touch me even if you could'). … It's a story of two people getting together and then separating and then realizing through that separation that what they needed in life was each other."
• Justin Key directed the music video, which is set in the 1980s and retells the song's story. Brandon Lancaster explained to CMT why this particular song and video is so special to him.
  
  "Love is a journey," he said. "It's not this momentary thing. This song is taking you through a journey. That's what love actually is, and if you're going to have a love song, it's cool to have one that isn't as momentary and talks about people changing and having distance between each other and being confident and then not being confident."
  
  "And as a songwriter, those are the things you should be able to talk about, because that is real life," Lancaster continued. "In this specific song, it's narrated through two people who find each other really young, but the most interesting thing is that they're two people going through different phases of life. But they still end up finding love with each other. That's why this video is special to me. It's a real story."
• The song was played during the "There Goes My Life" episode of the Netflix series The Ranch.
• The song topped the Country chart for the week dated December 9, 2017.
• As Brandon Lancaster started writing the song he began to reflect on some of his experiences, including how he met his now-wife, Tiffany Trotter. He explained to The Boot:
  
  "I'm married now. I had been dating my wife since I was 19, so it wasn't necessarily high school. We had been together a long time, and took some time apart and broke up and got back together.
  
  The foundation of the song was from my life. I took some stories and some characters from my experiences growing up in Smyrna, [Tennessee], and some friends I had, a little bit of their story, and kind of put it all into one song. It's cool, because it's an ode to songwriting being both experiencing and observing, so that song has both of those things in it.
  
  Love is about compromise, and it's about meeting each other in the middle and learning about each other and learning about yourself through that person. One thing that's cool is, I think, now that I'm married – 'Greatest Love Story' is kind of about the story of that journey of finding love and finding that person, but now, being married, it's the beginning of another story, the beginning of another chapter. It's the end of one chapter, the beginning of the other, from a songwriting perspective."