Songfacts®:

• There are paper umbrellas in the world that serve a practical function. Some are even made to be water-resistant, designed for actual use in the rain. But clearly that's not what Tim McGraw is talking about here. No, the kind of paper umbrellas he's referring to are the tiny, decorative ones perched atop cocktails, the sort that immediately conjure images of tiki bars, pineapple-shaped drinkware, and questionable life choices.
  
  In "Paper Umbrellas," McGraw tells a tale of post-breakup reflection wrapped around the biting line, "Paper umbrellas look good on top, but they won't stop the rain." It's a hard truth, really - a poetic way of saying that drowning your sorrows in a mai tai isn't going to mend a broken heart.
• The song sets the scene with McGraw ducking into a tiki bar to escape a storm, only to find himself in the company of a woman spinning pink and yellow paper umbrellas between her fingers. She is, quite evidently, in distress - the unmistakable kind that follows romantic misfortune. And rather than viewing this as an opportunity to make a move, McGraw recognizes her pain and sees she needs a friend to talk to.
• Monty Criswell (George Strait's "I Saw God Today," Parker McCollum's "Handle On You") and singer-songwriter and actor Drake Milligan wrote the song. Milligan has a strikingly Elvis résumé, having portrayed the King on both the CMT series Sun Records and a young teen Elvis in the film Nobody. His own career as a recording artist has also seen success, particularly in Canada, where his 2023 single "Honky Tonkin' About" - recorded with country duo The Reklaws - topped the chart.
• Drawing from the universal experience of heartbreak and the need for solace, Criswell and Milligan shaped "Paper Umbrellas" into a song that champions genuine human connection over temporary escapes like alcohol. This theme fits seamlessly within McGraw's repertoire of deeply emotional, life-affirming songs, alongside numbers like "Please Remember Me," "Live Like You Were Dying," "Better Than I Used to Be," and "Humble And Kind."
• Produced by McGraw and his longtime collaborator Byron Gallimore, "Paper Umbrellas" blends neo-traditional country with a subtle island feel - just enough to remind you that, yes, there's probably a piña colada somewhere in this story.
• The song found its home on McGraw's 2023 album Standing Room Only, a project conceived during the pandemic when, unable to tour in support of his previous record, Here on Earth, he channeled his pent-up energy into songs that dug deeper into the messiness of being human.
• On March 7, 2025, McGraw refreshed "Paper Umbrellas" by bringing Parker McCollum into the mix for an updated version. Musically, nothing changed. The only difference? McCollum stepped in to sing some lines from the second verse onward.
• Parker McCollum went full fanboy when Tim McGraw asked him to sing on "Paper Umbrellas."
  
  "He asked me to do it quite a while ago - like a long time ago - and then nothing came of it," McCollum told Taste of Country Nights in July 2025. Thinking maybe the country legend had quietly moved on, McCollum let it go.
  
  Then came the call. "A few months ago, he reached back out and asked if I would sing on the song," McCollum said. "I was in the studio working on my own record, so I popped in the booth one day and put a few takes on it."
  
  It was a surreal moment for McCollum, a lifelong McGraw fan. "It was a big honor," he said. "I've been a Tim McGraw fan my whole life, so it was really cool."
  
  McCollum gave McGraw an easy out: "Hey, if you don't like it, you're not going to hurt my feelings. Don't sacrifice the song just to be nice to me."
  
  Clearly, McGraw liked it just fine.