He’s Had 33 No. 1s — But Kenny Chesney’s Still Mad About This One That Got Away

You don’t sell over 100 million records, headline stadium tours for decades, and land in the Country Music Hall of Fame without stacking up a few No. 1 hits — and Kenny Chesney has 33 of them.

But as it turns out, that might not even be the most impressive stat on his résumé.

“I’ve had more No. 2 records than probably any act in the world,” Chesney joked in a recent chat with Bobby Bones — though he wasn’t entirely kidding.

He continued, “I mean, I’ve had like 14 or 15 songs that didn’t hit No. 1 that were No. 2.”

Read More: Kenny Chesney Picks His Favorite Of His Songs: ‘It’s a Portrait of My Soul’

He’s not wrong. On the Billboard Hot Country Songs chart alone, Chesney has 12 No. 2 hits. And while most artists would dream of those kinds of "almosts," there’s one near-miss that still gets under his skin.

The One That Got Stuck

“No Shoes, No Shirt, No Problems” is more than just a hit — it’s a mantra, a fanbase, a way of life. However, in 2003, it stalled just shy of the top spot, held back by a beachy juggernaut from Alan Jackson and Jimmy Buffett.

“It got stuck behind my friend Jimmy Buffett and Alan Jackson’s ‘Five O’Clock Somewhere’ for eight straight weeks,” Chesney recalled. “Same label. Pissed me off, but that record was so hot, they couldn’t maneuver it.”

That rare behind-the-scenes confession — about how labels sometimes hold or push certain songs for chart strategy — reveals what country fans don’t often get to hear out loud.

Of course, there’s no bad blood. Chesney and Buffett were close friends until Buffett died in 2023, and the No Shoes Nation has love for both artists' island-country sound.

Still on Top

With a Hall of Fame plaque on the wall and a sold-out summer tour ahead, Chesney isn’t sweating the stats.

But don’t be surprised if “No Shoes, No Shirt, No Problems” still hits a little harder live. That one still means something — even if it never officially hit No. 1.

The Runner-Ups That Still Hit the Feels

Chesney’s not exaggerating — the man has a stacked roster of No. 2 hits, including fan favorites like:

“Knowing You” (2021)

“Happy Does” (2020)

“Shiftwork” (with George Strait, 2007)

“Who You’d Be Today” (2005)

“The Woman With You” (2004)

“I Go Back” (2004)

“Big Star” (2003)

“Young” (2001)

“That’s Why I’m Here” (1998)

“When I Close My Eyes” (1996)

“Me and You” (1996)

Yes, some of these reached No. 1 on the Country Airplay chart — but for Chesney, the Hot Country Songs chart is where the magic counts.