Kenny Chesney’s Best Albums

Mar 28, 2022


Kristen Humphries

With almost 30 years in the music industry, 24 albums, and 19 headlining tours, Kenny Chesney is one of country music’s longstanding biggest names. After two years of COVID-19 cancellations, Chesney sets out on the “Here and Now Tour 2022” with Dan + Shay, Old Dominion, and Carly Peace in late April. Aside from his music, Chesney has his own rum (Blue Chair Bay™), a SiriusXM radio show (No Shoes Radio), and a grassroots ocean conversation project (No Shoes Reefs). 

I grew up with a Kenny Chesney-obsessed dad playing CMT music videos on the TV every Sunday morning. According to him, “[Chesney’s] songs generally send a down-to-earth, positive message and his shows exude so much energy, the atmosphere is electric.” And I believe it. Though I consider myself only a mild country fan, I’ll try to honor Chesney’s legacy by choosing — what I believe to be — his best albums. Let me know if I got it right?

When The Sun Goes Down (2004)

Beach vibes, love songs, and an ounce of nostalgia — what else would you expect from a Kenny Chesney album? Even non-Chesney fans know the track title “When The Sun Goes Down (feat. Uncle Kracker).” Much like Chesney’s entire discography, the album title is an ode to the summer months, warm weather, and beach life. Songs that follow suit are “Keg in the Closet” and “Outta Here.” For the hometown lovers and the youth-nostalgics, “There Goes My Life” and “I Go back” hit like a train. The former, written by Wendell Mobley and Neil Thrasher, is a stark opening choice to an otherwise upbeat record. As a former athlete, the chorus in “I Go Back” sends me right back to high school (not that I would otherwise choose to revisit). When The Sun Goes Down is your go-to for both tailgate anthems and road trip relaxers. 

Be As You Are (2005)

Chesney calls Be As You Are the “island album,” which fits the stripped-back, acoustic, reggae-influenced 13 tracks. He taps into the daydream of beach life, slowing down from the mundane nine-to-five reality in an album. “Guitars and Tiki Bars,” “Island Boy,” “Somewhere in the Sun,” and “Key Lime Pie” are obvious nods to the islands with that easy listening, closed-eyes-on-the-beach type of feeling. If you’re looking for a summer album designed for a tropical location and relaxation, Be As You Are is for you. Composed mostly of ballads, the album qualified for RIAA Platinum and earned Chesney a prestigious Triple-Crown Award presented by the Academy of Country Music. 

No Shoes, No Shirt, No Problems (2002)

In slight contrast to Be As You Are, Chesney’s 2002 release No Shoes, No Shirt, No Problems packs uptempo hits and soft ballads into one cohesive project. The album’s first single “Young” peaked at number two, while its successor “The Good Stuff” spent seven weeks at number one, becoming Billboard’s number one country song of the year for 2002. One of my personal favorites off the album is “Big Star” (and not just because Chesney and Taylor Swift performed it in Nashville twice) — a song about a woman succeeding in music thanks to hard work and passion. Other highlights include “On the Coast of Somewhere Beautiful,” a perfect song for watching the sunset on — you guessed it — the coast, and “Live Those Songs,” one of my favorite choruses on the entire record.

The Road and The Radio (2005)

Every single from The Road and The Radio reached the Top 10 on the U.S. Billboard Hot Country Songs chart. “Living in Fast Forward,” “Summertime,” and “Beer in Mexico” all hit number one. Similar to When The Sun Goes Down, Chesney’s tenth album The Road and The Radio is a combo of melodic country hits and laidback storytelling. I still hear “Summertime” and “Beer In Mexico” playing from my parents’ porch when I stop by in the warmer months. Much like his previous work, Chesney’s The Road and The Radio is an easy listen — perfect for the first day of summer, a long drive on the highway, and especially, a night out with friends.

Hemingway’s Whiskey (2010)

Some of my all-time favorite Chesney songs are on this album: “You and Tequila (feat. Grace Potter),” and “Somewhere With You.” To me, this was Chesney’s first album that invited non-country fans to his music. Maybe it was Grace Potter’s backing vocals in “You and Tequila,” but the song reached a new audience and set Chesney apart from the typical country artist. “Somewhere With You” did the same — if you replaced Chesney’s vocals with a rock artist, both songs would be considered rock. It’s this reason I feel Hemingway’s Whiskey is one of Chesney’s most widely-accepted albums from non-country fans. On the flip side, “Reality” hit number one on the Hot Country Songs chart and is a straightforward Kenny Chesney song about escaping reality and what that means individually for everyone listening. For him, “It’s a beach bar / Or on a boat underneath the stars / Or with my band up on a stage.