Back from retirement again, the polarizing, meme-powered pop singer takes up “cowboy emo”: breakup songs with a cartoonish twang and schlocky Western aesthetics.
Oliver Tree swore he wouldn’t make another album, but here he is, howling away on Jimmy Kimmel Live, taking off his big blue cowboy hat to reveal a series of smaller cowboy hats. This is Tree’s schtick: inane gimmicks that overshadow his music and even his blatant pleas for streams. In recent months, he’s crowned himself the “Vape God” from a bathtub full of e-cigarettes and boasted of spending $20,000 on tinfoil twisted into the shape of an octopus. He promoted his new album’s first single, “Cowboys Don’t Cry,” by claiming his label wouldn’t release the track until 100,000 people pre-saved it. “I’m not good at goodbyes,” he wails at the top of the song—the same phrase he used back when he announced his “retirement.” It was a wink and a middle finger to fans who got the reference, a rebuke for anyone who took him at his word.
Cowboy Tears represents a new era for Tree’s sound and style, as he trades the synth throb of 2020’s Ugly Is Beautiful for a cartoonish twang and schlocky Western aesthetics. “Just an outlaw who only had one friend,” he proclaims on the opener. He calls this “cowboy emo” music, a mix that comes across more like an emoji mashup than a cohesive mesh of genres. There are twinges of acoustic folk (“Swing & A Miss,” “California”), but more often Tree borrows from 2010s pop-rock, with sludgy distortion and reverberating whines. “I was chasing the sound of a song I heard in a Taco Bell when I was five years old,” Tree, 28, said of the album. He comes closer to the shaggy sounds of Grouplove doing their best Pixies impression, or Cage the Elephant mimicking Modest Mouse. Travis Barker offers his requisite stamp on any TikToker-turned-artist’s album, and Tree’s nasally snarls tip into Machine Gun Kelly cosplay, especially on the Barker-produced “Cigarettes.”
Eager to convince his audience that absurdity is inherently nuanced, Tree defaults to disgust. On “Cigarettes,” he crams 20 cigs into his mouth at once. On “Playing With Fire,” he moans about “drool hanging down from my double chin.” “I’m a weirdo, I’m a freak,” he proclaims on “Freaks & Geeks,” with the sincerity of a Riverdale monologue. On “Suitcase Filled With Cash,” he narrates a pile of burning money by the side of the road, a supposed statement that’s more chirpy campfire singalong than anti-consumerist anthem. “Some people are so poor that all they have is money,” he wails. For all this gesturing at subversion, Tree stays within his comfort zone: Many other songs are breakup ballads with a side of country imagery and generic lyrics that leave the listener filling the blanks (“I miss the things we used to do,” he hollers on one; “Riding ’round this wagon wheel, if you catch my drift,” he croons on another).
Tree told an interviewer that his study of Pink Floyd inspired him to tackle the album’s range of weighty themes. According to Tree, these include “money, time, religion and addiction,” motifs that rarely manifest in the actual lyrics. There is a darkness underpinning Cowboy Tears: jarring asides about Tree’s longing for death and plans for his own burial. He never lingers long enough to elucidate whether they’re more than just a facet of a melancholy “emo” aesthetic. Even when he grasps at a compelling concept—like presenting “Cowboys Don’t Cry” as a challenge to traditional masculinity—he never fleshes out a narrative or truly articulates a stance. His character’s main trait is a lack of substance; the songs are almost an afterthought in the project of performing Oliver Tree. There’s only one real surprise on Cowboy Tears, a little pulse of self-awareness as he breaks through the fourth wall. “I’m a dumbass, but people love that,” he sings on “Freaks & Geeks,” sounding a little weary of the charade, a little sick of his own bullshit. But he couldn’t be Oliver Tree without it.
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