The Journey Of ‘Down The Road’ By Kenny Chesney and Mac McAnally

The track was written and originally recorded by McAnally and later became a chart-topping hit when Chesney and McAnally recorded it as a duet.


Melanie Rooten

| Posted on

February 28, 2024


10:09 am

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Kenny Chesney and Mac McAnally; Photo by Kayla Schoen/CMA

Kenny Chesney and Mac McAnally made waves within the country music industry with their collaborative version of McAnally’s “Down The Road,” released on November 10, 2008 and peaking at No.1 on this day in 2009.

As the song continues to resonate with fans, many may be wondering how exactly “Down The Road” came to be, and fortunately, Country Now took a deep dive into the origin and overall meaning of the chart-topping tune. 

Mac McAnally Was First To Release The Song

“Down the Road” began as a solo song by Mac McAnally, originally released as the second single from his 1990 album titled Simple Life, and released a second time as a part of his 1994 album titled Knots.

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Within this track, the narrator describes his childhood love interest – who happens to live right “down the road” – as well as the expectations that her parents set for him. Within the song, the narrator transitions from being a child to being an adult, and the tables have turned as his daughter now has a love interest who happens to live right “down the road” as well. Towards the end of the tune, the narrator is the adult setting expectations for his daughter’s lover instead, ultimately creating a song jam-packed with parallels. 

In an interview with The Boot, McAnally dished about his experience writing the song, which began on Christmas morning after thinking about what the lives of his daughters would be like in the future.

He Wrote The Song On Christmas Morning

“It was a very organic little song, written on Christmas morning 1987. I was putting together some stuff that wasn’t supposed to require assembly. Turned out I needed some D batteries at 3 o’clock in the morning in Sheffield, Alabama. I don’t recommend that as a scavenger hunt item! I finally got everything done, and it was close enough to daylight that I decided just to sit out on the porch and wait until the kids got up to see what was under the tree… I wrote this little song, and it was its own reward… years ago,” he explained.

Peaking at number 70 on the Billboard Hot Country Songs chart, this terrific tune did not achieve as much success as it deserved, that is until Kenny Chesney entered the picture 18 years later. 

Kenny Chesney, Mac McAnally; Photo Courtesy of CMA
Kenny Chesney, Mac McAnally; Photo Courtesy of CMA

“Down the Road” Featuring Kenny Chesney

As a part of Chesney’s 2008 album titled Lucky Old Sun, Chesney and McAnally teamed up to record a duet of “Down the Road,” with the latter singing the second verse and chorus.

While McAnally’s version is known for its electric guitar riffs throughout the track, Chesney’s version is much more scaled back as far as production– featuring only two steel-string acoustic guitars and congas – but fortunately, this new sound worked in their favor, garnering a great deal of success. 

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Chart Success

The collaborative version of “Down The Road” made its debut at number 59 on the country charts, falling off the charts and re-entering at number 38 for the week of November 15. This tune ultimately reached number one on February 28, 2009, marking Chesney’s sixteenth number one and McAnally’s first and only number one to date.

To top it off, Chesney and McAnally were also nominated for a GRAMMY Award in 2010 for Best Country Collaboration with Vocals, however, they ultimately fell short to “I Told You So” by Carrie Underwood and Randy Travis.

Nonetheless, both Chesney and McAnally’s versions of “Down The Road” are available to stream on all platforms, even decades later. 

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Melanie Rooten

Written by

Melanie Rooten

Originally from Southern California and currently residing in Music City, Melanie graduated from the University of Oklahoma with a BA in Journalism before beginning her career as a music and entertainment journalist. Beginning to write for Country Now in August of 2023, she has also contributed to Holler, Music Mayhem, Country Chord, Celeb Secrets, Celeb Secrets Country, We Got This Covered and Decider throughout her career thus far. When she is not writing, Melanie enjoys going to concerts and music festivals, binging her favorite television shows, spending time with her friends and family and cheering on the Oklahoma Sooners (of course).