Chris Stapleton’s Albums Ranked Worst To Best

It’s no stretch to say that Chris Stapleton is a legend in the making. From his jaw-dropping vocals to his diverse songwriting history, it truly seems like there’s nothing that the Parachute singer can’t do musically.

The reigning ACM Entertainer of the Year winner released his fifth studio album, Higher, back in November. Now that some time has passed and Higher has been given time to digest, there’s no better time to rank all of Stapleton’s albums.

Without further ado, here is my ranking.

5. Higher

I’d like to preface this ranking with the fact that Higher has the disadvantage of being out the least amount of time compared to the rest of Stapleton’s records as previously mentioned. That being said, I simply don’t think it is as strong as the rest of his deep discography from a song-to-song standpoint.

I do respect the fact that this record is laser-focused on being a tribute to his wife, Morgane. It’s a very love-song-heavy record that shockingly doesn’t get too tiring given the lack of lyrical variety throughout the album. That being said, you do feel the lack of variety a bit, especially towards the end of the record.

While some may dislike Stapleton leaning into his R&B sensibilities on tracks like Think I’m In Love With You, Loving You On My Mind and Higher, they are some of the most interesting songs on the album both sonically and vocally. He’s really stretching his vocal range on these tracks, and the results are nothing short of incredible.

Standout Track: Think I’m In Love With You

4. From A Room: Volume 1

It’s no small task to attempt to follow up on a record as groundbreaking and popular as Traveler. While From A Room: Volume 1 is by no means a bad or even average album, I often find myself skipping over a majority of the songs present on the record in comparison to the rest of Stapleton’s discography.

There are some incredibly high highs on Volume One. The #1 hit, Broken Halos, the jaw-dropping Either Way and the bluesy ode to cannabis, Them Stems, are the clear standouts on the album and once again showcase how diverse Stapleton’s writing ability is.

There’s truly nothing wrong with the rest of the album; it’s not like there are any bad songs present. The only issue present is the simple fact that Stapleton has so many great tracks on other records that From A Room: Volume 1 ultimately gets a bit overshadowed as a whole.

Standout Track: Either Way

3. From A Room: Volume 2

Coming in just above its predecessor is From A Room: Volume 2. The album, overall, feels a bit more balanced and memorable than Volume 1, playing with a lot of different sounds and styles throughout its runtime.

You get Stapleton’s traditional sensibilities on Millionaire and Simple Song, his Southern rock influences on Midnight Train to Memphis and Hard Livin‘ and even a bit of Irish folk on Scarecrow In the Garden.

To me, Stapleton is at his best when he’s balancing his lighter, introspective tracks with his heavier, rockin’ songs, and in From A Room: Volume 2, he does this incredibly well.

Like Vol 1., the record comes in at nine songs and just over 30 minutes, but this one flies by in comparison due to the expertly paced tracklist that balances out the sonic highs and the lows of the record beautifully.

Standout Track: Scarecrow In the Garden

2. Starting Over

Simply put, you don’t sweep the CMA, ACM and Grammy Awards for best album by accident. Starting Over feels like one of those once-in-a-lifetime records, and it’s still not #1 on this list. If that doesn’t exemplify the fact that Stapleton has a real chance of being one of the greatest country artists ever, I don’t know what does.

It’s on Starting Over that Stapleton fully realizes his seemingly dual nature as an artist. He is equally a passionate lover as he is a rambling man. You got this sense of duality on Traveller, and it is explored even more here.

Stapleton does a fantastic job with the aforementioned concept throughout the album’s tracklist. He pens gorgeous, loving songs such as the title track, When I’m with You, Joy of My Life while simultaneously balancing them out with some rockin’ tracks like Arkansas, Hillbilly Blood and Whiskey Sunrise.

This results in the album feeling much shorter than its 14-song, 54-minute runtime. Starting Over is an expertly-paced record that never feels like it’s going on too long mainly due to simply how many fantastic tracks he packed into the record.

Standout Track: Maggie’s Song

1. Traveller

What is there to say that hasn’t already been said about Traveller? Despite it only being seven years old as of writing this, it’s already widely recognized as one of the best country albums not only of the 2010s but of all time.

There’s a good reason for this claim. There are truly no weaknesses present throughout the album. The production is rock solid, incorporating traditional instrumentation with modern sensibilities, the lyrics are compelling albeit nothing too challenging and arguably most importantly, Stapleton’s vocals are nothing short of incredible.

No skip albums are incredibly hard to come by, but Traveller absolutely falls into that category. There are no forgettable tracks throughout the record, with each song building off of the next one and expanding an extremely lived-in world that Stapleton created here.

There are so many different highs throughout the record; it’s hard to truly point out a definitive one. Some may point to his iconic cover of Tennessee Whiskey as the high. Others may point out the devastating Fire Away as the high. There’s really no wrong answer, and that’s what makes Traveller such a special album.

Further proving how special of an album Traveller is, Tennessee Whiskey was never officially released as a single. Despite this, with the combined popularity of both the single and the album itself, Tennessee Whiskey is currently 14x platinum. The legs that this album has had over the past seven years sales and popularity-wise is nothing short of incredible.

Standout Track: Fire Away