If you read some interviews featuring the extravagant and eccentric performance artist and living meme that is Oliver Tree, you’ll know that he never intended to pursue music as his main artistic pursuit for long. You’ll also know that it’s impossible to trust nearly anything he says, as it all eventually works its way around to playing a small role in the bigger picture of a huge joke. Even so, Oliver Tree’s latest, Cowboy Tears, feels like it’s a lot more personal than it’s ever been, revealing the real guy behind all of the prosthetics, costumes and bombast – so when he says this is his last album, for real this time, it’s actually easier to believe him.

Following a breakup with fellow oddball singer Melanie Martinez, Tree will tell you the story that he relocated to his grandfather’s ranch to process his emotions, having recently retired from music, upon which a country album manifested much to his surprise. The resulting album isn’t country – in fact, it’s a lot more of the same when it comes to Tree’s brand of 90s nostalgia-fuelled mashups of pop-rock, hip-hop and electronica formulae, all topped off with his obnoxiously nasal singing voice – but it does contain a lot of unexpectedly poignant messages about toxic masculinity and bottling your feelings up until it’s too late. For all of the transgressive art that Tree creates, however, it’s still as difficult as ever to fathom why his music is anything but. For Tree, it’s always been more of a means to an end – there are a lot of interesting things to discover about his new artistic venture, but not many of them are on the album itself.

The album’s opening track “Cowboys Don’t Cry” might be the best song Tree has ever made from a musical standpoint, featuring the closest thing here to genuinely country instrumentation with some slide guitars, bright acoustic chords and some lyrical nodes to outlaws and the like. Tree drops some clever lyrical references to his former partner’s work to clue in those in the know, and hearing some genuine emotions with a tangible backstory that we know is completely real is a truly powerful experience from the guy who usually rambles on about scooters. The big drum hits and some genuinely great harmonies complement one of the nicest melodies here, before things get more repetitive and tiresome. “Swing & A Miss,” like many of the tracks here, feels like if Smash Mouth, Sugar Ray, Weezer and just about any other of the goofy pop-rock bands full of white guys with soul patches and huge smiles in the 90s mashed all their greatest hits into one – complete with the DJ scratches for an ironic nod to hip-hop culture – and gave it to a guy with worse vocals. It’s fun to hear the sounds come together for the first time, and this track does have a fuller, warmer sound than most, but many of the instrumentals on the remainder of the project tread the same ground. “Freaks & Geeks” sees him play up his annoying vocals even more, delivering a nasal, spoken word passage about being an outsider as he steps into a character before the song delivers a tonally awkward juxtaposition with a throaty, belted alt-rock hook.

The 90s pastiche of sounds continues onto the track “Doormat,” which sounds hilariously similar to Sugar Ray’s “When It’s Over” in terms of both its melody and instrumentation – of course, that song is an enduring hit single for a reason, and the falsetto “whoo-hoos” and general stadium energy that Tree infuses this track with taps into such a specific area of nostalgia and pulls it off shockingly well, his borderline emo inflections wringing every little bit of drama out of a line like “you kicked me around like a pile ‘a traaaash.” The tracks “Suitcase Full of Cash” and “Cigarettes” continue to tread similar instrumental ground, Tree not offering much to return to in the way of the actual music, but when the music videos, his true specialty, are eventually released, we should be seeing these more poignant narrative tracks reach their full potential. “Cash” is a carefree, beachside ode to boundless creativity, advising listeners to make art for the sake of it rather than the monetary gain, while “Cigarettes” sees him playing a highly concerning narrator who is hopefully one of his characters as he tells a tale of fatal addiction. Following up on the album’s theme, the narrator probably needed a good cry instead of numbing himself out of his mind, Tree as usual juxtaposing something highly concerning and dark with clownish delivery and in-your-face music as the guitars get heavier.

As the album stretches into its back half, some of Tree’s biggest musical weaknesses begin to show themselves and throw off the enjoyment of the themes on display. “Balloon Boy” and “California” both contain some cringeworthy off-key singing performances, and the disturbing imagery as he describes the experience of dying and sing-songy melody of the former makes it even harder to sit through, especially when Tree backs himself up by singing an octave higher when he couldn’t even nail the original. “California” is a lot more personal and heartfelt, as Tree talks about the comfort of his hometown and the overwhelming Hollywood lifestyle he’s stepped into, but his lack of musical abilities makes it difficult to stomach for an active listener. The track “Things We Used To Do,” sandwiched in between, continues to display his knack for a supremely catchy hook, despite the exact same instrumental techniques used behind it right down to the two DJ scratches to introduce a hip-hop beat. While Tree’s lyrics get a little more concerning – especially knowing that they’re a lot more grounded in reality – as he tries desperately to win his old relationship back by threatening unhinged and fatal consequences, the themes of the album tell us that Tree is making an important statement: that it’s better to exorcise those demons through self-expression than to keep them inside and one day act on them.

The tracks “Get Well Soon” and “Playing with Fire” continue what sound like Tree’s direct addresses to Martinez, the latter seeming like it’s gesturing at suicidal ideation if she doesn’t take him back while the former laments that she has her own mental health issues to work through that prevented things from working out. It’s certainly a lot to sit through, and Tree has some big, cinematic ideas here that might translate better in the movies he wants to make in the future. “Get Well Soon” does come equipped with an innovative section of chopped-up vocals substituting for a chorus, but it’s going to be hard to return to these. The album fades out on “The Villain,” featuring another great, cathartic chorus that’s ready for the swinging lighters and a swung tempo to switch things up, and title track “Cowboy Tears,” one of the heaviest tracks here where he reiterates that it’s okay to cry.

Oliver Tree, as he’ll tell you himself, is a lot more than just music – it’s kind of just where he accidentally ended up in his pursuit of all things creative. If this is really the end of the road, it’s likely going to get a lot more exciting from here in whatever he does next.

Favourite Tracks: Cowboys Don’t Cry, Doormat, The Villain, Cigarettes

Least Favourite Track: Balloon Boy

Score: 5/10