Ever been at a bar, spotted an old flame, and felt that weird mix of "I shouldn't" and "I really want to"? That’s exactly where Josh Ross Single Again was born. It wasn't some manufactured Nashville writing room concept. It was a real night out. A real high school crush. And a very real, slightly awkward conversation that turned into a multi-platinum career milestone.
Timing is a funny thing in country music. Sometimes you release a song and it vanishes. Other times, you capture a specific flavor of heartbreak that everyone—and I mean everyone—has tasted.
The High School Crush That Started It All
Honestly, the backstory is kinda legendary at this point. Josh was out at a bar when he ran into a girl he used to have a massive crush on back in high school. He did what any guy would do: he tried to buy her a drink.
She turned him down. She had a boyfriend.
But instead of just walking away, Josh dropped the line that would eventually top the charts: "Well, let me know if you’re ever single again."
He didn't write the song that night. He sat on that memory. He let it marinate until he got into a room with Joe Fox and Brad Rempel. They took that raw, somewhat cheeky moment and turned it into a "bold barroom anthem."
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Why Single Again Josh Ross Hit Different in 2025
By July 2025, this track did something no Canadian male country artist had done in nearly thirty years. It hit No. 1 on the U.S. Mediabase Country chart. The last guy to pull that off? Paul Brandt back in the mid-90s.
It’s a long road to the top. 71 weeks, to be exact.
People think hits happen overnight. They don’t. This song climbed the charts like a slow-moving freight train, picking up steam until it became the most played song in America. Josh has talked about how he used to come to Nashville in 2018 just hoping to hear anything he wrote on the radio. Now, he’s got a custom Taylor 210e DLX guitar from BMI to commemorate his first No. 1.
The Sound: Rock Meets Hushed Vocals
There's a specific "Josh Ross" sound that makes this track work. It’s got that modern country-rock edge, but his voice has this warm, raspy quality. It sounds like he’s actually lived the lyrics.
- Produced by: Matt Geroux (the same guy behind "Trouble" and "Red Flags").
- Vibe: Moody, emotional, but still something you can blast in a truck.
- Success: RIAA Gold certified (500,000 units) as of December 2025.
From the Gridiron to the Grand Ole Opry
Josh wasn't always a singer. He was a football player first. A defensive back in college. You can still see that athlete mentality in how he handles his career. He treats touring like a season and the gym like a second home.
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He had to give up some things, though. He’s a big BMX fan, but he’s admitted he doesn't ride as much lately. Why? Because a broken arm or a wrecked shoulder would tank a tour. When you're opening for guys like Jelly Roll, Luke Bryan, and Bailey Zimmerman, you can't really afford to be in a cast.
What the Lyrics Actually Mean
While the "single again" hook is catchy, the song is really about the frustration of bad timing. It’s that "what if" that keeps you up at night.
In the official music video, directed by Jack Owens and shot in Franklin, Tennessee, you see this play out. It’s about a chance encounter sparking a connection that maybe shouldn't be there—or maybe it should have been there all along.
It’s a stark contrast to his other 2024 release, "Truck Girl," which is much more about the raw pain of someone walking away for good. Josh Ross Single Again is more about the hope—or the lingering possibility—of a second chance.
Breaking Down the 2026 Tour
If you're trying to catch him live to hear it in person, you've got plenty of chances. Josh is currently on his "Later Tonight Tour."
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- January 2026: He's playing Luke Bryan’s "Crash My Playa" in Cancun. Not a bad gig if you can get it.
- February-March 2026: A massive run through Canada, hitting Montreal, Ottawa, Toronto, and Vancouver.
- April-June 2026: He’s jumping on the Nate Smith "Long Live Country Rock & Roll Tour" across the U.S., with stops at Stagecoach and Tortuga Music Festival.
What Most People Get Wrong About the Song
A lot of fans think the song is a "happy" reunion track. It’s actually more complicated than that. It’s about the tension of waiting for someone else's relationship to fail so you can have your shot. It’s a bit selfish, a bit desperate, and very human.
That’s why it resonates.
It doesn't pretend to be a perfect love story. It’s a barroom story. It’s the kind of thing you tell your friends over a beer, wondering if you should have sent that text or if you should just leave well enough alone.
Actionable Takeaways for Fans
If you're following the rise of Josh Ross, there are a few things you should actually do to stay in the loop:
- Listen to the "Complicated" EP: This is where the song lives alongside "Truck Girl." It gives you the full picture of his 2024 transition.
- Watch the Live From London version: He recently released some live tracks in December 2025 that show off his vocal range better than the studio recordings.
- Check the 2026 Festival Circuit: He’s booked for almost every major country festival this summer. If you want the full "Single Again" experience, a festival crowd is the place to be.
- Follow the CCMA News: He’s a regular winner now, taking home Single of the Year and Video of the Year for this specific track.
The story of this song is proof that real-life moments make the best music. A rejected drink offer at a bar turned into a career-defining No. 1 hit. It just goes to show: sometimes, the "no" you get today is just setting up the "yes" for later tonight.