There is no definitive ranking of Chris Stapleton’s “best” songs, and their heartbreak takes different forms: grief, strain in a relationship, and the uncertainty of beginning again. The clearest meanings come from what Stapleton has said about writing them; other readings belong to the listener. One celebrated song in this selection is also a cover, not his composition.
“Maggie’s Song”: a goodbye shaped by grief
Stapleton gave this song a direct personal context: “I wrote that song the day after our dog, Maggie, passed away,” he told Georgia Public Broadcasting/NPR in an interview published November 13, 2020. Read the interview.
| # | Preview | Product | Price | |
|---|---|---|---|---|
| 1 |
![Traveller [2 LP]](https://m.media-amazon.com/images/I/51DE2ygk7iL._SL160_.jpg)
|
Traveller [2 LP] | $27.97 | Buy on Amazon |
| 2 |
|
Higher (2LP-Vinyl) | $50.99 | Buy on Amazon |
| 3 |
![Starting Over [2 LP]](https://m.media-amazon.com/images/I/31oCQkIXSCL._SL160_.jpg)
|
Starting Over [2 LP] | $42.99 | Buy on Amazon |
| 4 |
![From A Room: Volume 1 [LP]](https://m.media-amazon.com/images/I/51rHjqYzUDL._SL160_.jpg)
|
From A Room: Volume 1 [LP] | $28.99 | Buy on Amazon |
| 5 |
![Traveller [Cola Bottle Clear 2 LP] [Amazon Exclusive]](https://m.media-amazon.com/images/I/41iNNyCsVWL._SL160_.jpg)
|
Traveller [Cola Bottle Clear 2 LP] [Amazon Exclusive] | $37.99 | Buy on Amazon |
The Ringer reported that Maggie was 14 and that the song took about ten minutes to write, based on Stapleton’s recollections. The Ringer’s interview offers that added context. The account makes the song’s grief unusually clear, but it does not establish that every lyric is a literal record of events. Its power can be heard as a personal farewell without treating the song as documentary evidence.
“Fire Away”: commitment’s difficult side
Stapleton described “Fire Away” as “a song about the frustration of commitment to me,” in a report by American Songwriter published November 20, 2023. The song was co-written with Danny Green. American Songwriter’s report says Stapleton recalled that a possible argument shortly before the writing session may have fed the song, while also saying he did not remember much about writing it. That uncertainty matters: the remark about commitment is his stated interpretation, but the argument is not a confirmed, complete origin story.
#1 Best Overall
- Recorded at Nashville's historic RCA Studio A, with additional production at The Castle and Blackbird Studio, Traveller was produced by Dave Cobb (Sturgill Simpson, Jason Isbell) and recorded by Vance Powell (Jack White)
The song’s heartbreak is less a single loss than the friction of staying close to someone. That reading fits Stapleton’s description without turning a lyric into a claim about his private relationship.
“Starting Over”: hope with no guarantee
Stapleton described the song’s central idea to The Ringer: “There’s hope in having to start over. Within that idea, there’s the promise of making something a little better.” The interview appeared November 13, 2020. Read the interview.
Rank #2
- Current ACM Entertainer of the Year, Chris Stapleton is set to release his 5th studio album Higher on November 10, 2023
That hope does not require certainty that everything will work out. Starting again can mean accepting that the old arrangement has failed while still believing a better one is possible. The album was released in 2020, but the date alone does not show that the song was written in response to the pandemic.
“Tennessee Whiskey”: a love song Stapleton made his own
“Tennessee Whiskey” is on Traveller, but Stapleton did not write it. American Songwriter identifies Dean Dillon and Linda Hargrove as its writers and David Allan Coe with the 1981 hit. The report distinguishes that songwriting history from Stapleton’s version. Its devotion can be heard as a love-song declaration, but there is no basis here for treating it as a personal confession by Stapleton.
PC Slower Than It Used to Be?
A free scan shows the junk files, broken settings and background clutter dragging Windows down - then fixes them in one click.Free scan · Windows 10 & 11Outdated Drivers Are Slowing You Down
One free scan finds every outdated or missing driver and matches the right update for your exact hardware.Free scan · exact hardware matchRank #3
- Chris Stapleton to release his brand-new studio album, Starting Over, on November 13th
On January 12, 2026, Stapleton’s official site announced that the recording had received RIAA Double Diamond certification, reporting more than 20 million units sold and calling it the first country song to reach that milestone. Those figures and the “first” claim are the official announcement’s characterization. See the announcement on Stapleton’s official site.
“Broken Halos” and “Either Way”: readings, not confirmed origin stories
Both songs appear on From A Room: Volume 1, according to Stapleton’s official discography. The discography establishes their album placement, not a definitive interpretation of their lyrics. “Broken Halos” can be heard as a meditation on loss and the limits of understanding it; that is a listener’s reading, not a meaning statement attributed to Stapleton here.
Rank #4
- Chris Stapleton will be releasing his brand new record "From A Room: Volume 1" on May 5th
“Either Way” lends itself to a reading of a relationship nearing its end, where resignation and hurt coexist. iHeartRadio reported in 2017 that Stapleton had written it more than a decade before its release and later revived it partly because his wife and people he had played it for liked it. That account describes the song’s history, not an authoritative explanation of its meaning. Read the iHeartRadio interview.
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.Release context for the songs
Stapleton’s official discography lists the albums and tracks below. The dates identify album releases, not when each song was written.
| Album | Release date | Songs discussed here |
|---|---|---|
| Traveller | May 4, 2015 | “Tennessee Whiskey”; “Fire Away” |
| From A Room: Volume 1 | May 5, 2017 | “Broken Halos”; “Either Way” |
| Starting Over | November 13, 2020 | “Maggie’s Song”; “Starting Over” |
Dates and track placement are from Stapleton’s official discography. The selection here is organized by emotional subject and by what is established about each song, not by an objective “best” ranking.
Quick Recap
Product prices and availability are accurate as of the date/time indicated and are subject to change. Any price and availability information displayed on Amazon at the time of purchase will apply.
