Album Review – Jesse Daniel’s “Looks Like Rain”

Traditional Country (#510) on the Country DDS.

When Jesse Daniel first burst out onto the scene in 2018 with his self-titled album and one of his signature songs “Soft Spot (For the Hard Stuff),” he came with an inspiring story of how he was using country music as an avenue for rehabilitation and redemption. Daniel was easy to root for, especially as he delivered stellar boot scooters from subsequent albums inspired by the Bakersfield sound like “Rollin’ On” and “Think I’ll Stay.” They became unexpected cult hits from a strongly independent performer.

But Jesse Daniel just wasn’t in a place to compose honky tonk heaters when it came time to write and produce his latest album Looks Like Rain. He was in more of an introspective, singer/songwriter mood. This doesn’t come across in the musical accompaniment for these songs necessarily. That’s still decidedly country, even if slightly more sparse in certain songs. Its reflected in the attitude of the songs themselves, and how they take a more somber, inward, and at times, sullen approach, so much so that Jesse himself prefaced this record with almost a warning to not expect a boot scooting good time.

When the book is written on how country music was saved, Jesse Daniel won’t play an insignificant role. From converting listeners, to influencing peers, and even opening doors for some who would come after, Daniel went from completely underground to a leading voice in the independent movement. But like so many artists who were established before the whole Zach Bryan/Zach Top craze took off, they have to wonder why they haven’t reaped more of those rewards. And now with touring costs spiking and opportunities shrinking, it’s hard to know what the path forward looks like, even for someone like Jesse Daniel who’s already strongly established.

Jesse’s originally from the San Lorenzo Valley in California, and proudly so, including singing about it often. But he relocated to just south of Austin for a spell, believing this would be a better place to make base camp for a country career. Perhaps on paper, he was correct. But as you hear in one of the standout songs on Looks Like Rain called “I Don’t Belong,” Jesse talks about feeling like a foreigner, and no matter where he goes. No wonder he’s now relocated back to California.

“Always Labor Day” is a really touching track that seems to be about a friend passing on too soon. And even though the deceased might now be in a place where every day is part of a three-day weekend, that doesn’t mean the loss is any more tragic, and doesn’t leave those of us left behind in the 40-hour grind feeling guilty for not reading the signs, or doing more to step in. When you conclude the song “Deep Dark Tears” is probably about the loss of a dog—and the way the steel guitar so mercilessly goes to work on you—it’s pretty hard for life to not start imitating art.

The songs for this album were recorded during the same period his last album Son of the San Lorenzo (2025) was, but these were the ones from a darker place. Though Daniel characterized this album as “stripped down,” excellent and tasteful musical performances grace the moments of Looks Like Rain, courtesy of standouts like steel guitarist Caleb Melo, fiddle player Billy Contreras, and harmonica legend Charlie McCoy. Jesse produced the set himself, but highly-regarded producer and engineer Andrija Tokic was an accomplice in the recordings.

When you get to a song like the comparatively lively “Our Love Is Gonna Pull Us Through,” you don’t hear any of the “stripped down” approach Jesse talks about. “Intentional” might be a better descriptor of how this album was rendered, including in the really strong story song about hidden desire called “Desiree” that concludes the album.

The opening title track to Looks Like Rain was actually the closing track to Jesse Daniel’s debut record, which is a hard choice to argue against since it sets the mood for this more somber record well. Daniel has re-recorded other songs in the past, and as title tracks (Son of the San Lorenzo). But that leaves Looks Like Rain with only seven new songs. And yes, there isn’t that one strong “single” for the boot scooters that can be the gateway to more casual country fans, while Daniel also isn’t exactly exhibiting Townes or Isbell-level writing here either.

But Jesse Daniel is no longer the kid that has to prove himself. Nearly a decade into his career, he has to be thinking about the future, what kind of songs and legacy he wants to cultivate, and what his life looks like down the road. Does spending more days than not in a tour van, forgoing kids for another year, trying to hold onto a touring band, and living in foreign-feeling places like he sings about in “I Don’t Belong” really something he wants to continue to endure into the future?

Looks Like Rain might not have all the answers. But it captures Jesse Daniel staring into the teeth of tough questions, wrestling with some self-doubt, and being unafraid to express these vulnerabilities through his songs. He used country music to persevere through addiction and hardship, and came out victorious and whole. But what’s next? Maybe it’s a future with more meaningful songs, fulfilling a desire to be more than just a honky tonker. Or maybe, just like all of us, Daniel needed to process through some darker moments to persevere, see the light, and reset for a brighter and more balanced future.

8/10

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Stream/Download Looks Like Rain