If you told me a year ago that I’d be an Oliver Tree fan again, I would have asked you what act of God brought that change to happen. I was burnt out from seeing that tired cartoon-character outfit and bowl-cut hairstyle he wore everywhere, and when he said he was quitting music (It peeves me to no end when artists announce they are “quitting” only to start rolling out a new album weeks later) I hoped it was true. But Oliver Tree was the artist I could not evade. From billboards in Los Feliz on my way to work, to his collaborations with my favorite artists, to his viral songs on TikTok, he was purely inescapable. 

And then, with ~serendipitous~ card fraud locking me out of my Spotify account, and an email containing the new album from Tree’s publicist in my inbox, I found myself listening, and re-listening, to an album I liked more and more each time. Oliver has shed his 80s jacket and bell-bottom jeans for a blonde mullet and denim cowboy get-up. The original Oliver Tree is still there, but he’s evolved stylistically into a western version of himself, like a weird Pokemon evolving towards final form. He’s even bulked up- donning a muscle suit in all of his shirtless shots in his latest music videos. 

The rollout of the new album started on January 12th, on the heels of his TikTok song “Life Goes On” hitting fever-high levels of viral on TikTok that warranted its own remix and music video directed by none other than Cole Bennett. Trippie Redd, Ski Mask the Slump God and Diplo featured on the bassified, reverbed-out mix. Oliver Tree, staying on brand with his quirks, rightfully casted The Island Boys as his security in the “Life Goes On” music video. Diplo and Oliver also started a “fake beef” with each other at the Super Bowl over Oliver cutting Diplo out of his photos with Flavortown legend, Guy Fieri. 

Oliver manages to disguise his talent as a writer with his goofy and insecure cover as Indie Pop’s goofy comedian. If you really dial into what he’s saying, it’s obvious Tree has potential to go deeper with his lyricism and develop a legacy of songs that are more memorable than his costume. This album takes its spot among the likes of Orville Peck, Lil Nas X and Diplo (who released an electro-country compilation album of his own in 2020 called Snake Oil) in the Yeehaw Agenda as it continues to rock music and fashion trends. 

Getting into Cowboy Tears, an album that’s been two years in the making, it’s clear that behind all of Oliver’s stunts, quirks, and his “kermit the frog voice” (stated by Diplo) is a multi-talented songwriter, entertainer and person who still goes through normal things like break-ups, trying to quit cigarettes, and missing home. The album touches upon these themes and other rights of passage told through the lens of an artist living behind a bit. On “Cigarettes”, co-written and produced by Travis Barker, Oliver plays out the consequences of smoking. Although he stated he’s one year clean from smoking in an instagram caption, he mimes lighting entire packs of cigarettes in his mouth in several of his latest music videos. “Smoke ‘em when I want/ lately that’s a lot” Oliver regretfully sings about his habits. The song “California”, a cut that sounds like the pledge of allegiance with a little *spice*, is an ode to his home state that we can assume he wrote while he was exploring the Middle East and Northern Africa and finishing his album. 

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The entire album is done with a plucky acoustic guitar complemented by thoughtful production. Most of the songs use minimal to no drums (or beats), and rely on record-scratch breakdowns, vocal-chop and keys. When beats are used, it's generally to amplify a chorus or a moment of spectacular production. “Get Well Soon” starts entirely with guitar and bass, then unexpectedly segues into a complete breakdown involving the alteration of his voice into the beat that devolves twice over into a final outro that sounds entirely euphoric. He has a similarly enjoyable breakdown in his earlier-released single, “Freaks & Geeks”, co-produced by Whethan, Oliver Tree and Casey Mattson. 

The four arguably strongest songs on the album aside from the well-received singles released earlier in the month, “Cowboys Don’t Cry” and “Freaks & Geeks”, are “Swing & A Miss”, “Get Well Soon”, “Cigarettes” and “Suitcase Full of Cash”. “Swing & A Miss' sounds like early 2000s rock and folk that feels like it would sync perfectly into the sad part of a rom-com. Oliver’s doleful voice bumbles over the guitar about disappointment like a tumbleweed through the California chaparral. Feels like he’s partially parodying himself with his haphazard vocals that convey his low state and sadness. “Suitcase Full of Cash” is where Oliver Tree really sees the payoff to his commitment to the bit. The song opens with a cop speaking into his radio, narrating Oliver’s debauchery as he sings about materialism, innovating an otherwise redundant theme. “We don’t care what you earn/ take your money, let it burn”, Oliver croons in between record-scratches. The constant ad libs have a very Green Day, punk sort of sound that's softened by his lyrics and background guitar.

The transition to a western-themed album is unsurprising considering how similar it naturally feels to a lot of his old music, but perhaps unintendedly, I started drawing other musical comparisons to the indie pop star. The tone and humor in the new album is reminiscent of Blink 182 and Weird Al Yankovic, music-comedy crossover legends of the millennial generation. Cowboy Tears may be a bit more genuine and dialed-back from his previous work, but it’s a step forward for the comedy musician and shows off a host of his musical chops that frankly, I was unaware that he possessed. And after my seventh listen of the damn album, I can confidently say Oliver Tree has won me back with his innovation, his outlandish music videos, and his vulnerability.

Oliver Tree launches the first night of his “Cowboy Tears” tour on Saturday in Los Angeles with 347aidan and Sueco along for the ride. Oliver’s “Meme Museum” pop-up will be happening tomorrow in LA on Fairfax Avenue. You can buy tickets to the tour here.

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