Oliver Tree Teases Yet Another Retirement and "The End of the Line" for Him (EXCLUSIVE)

Is Oliver Tree really retiring? He has announced retirement from music multiple times before and his fans are curious about how serious he is.

Chrissy Bobic - Author

Aug. 9 2022, Published 2:33 p.m. ET

If you're someone who has followed singer Oliver Tree for the past 10 years or the past two years, you understand that he's known for claiming an impending retirement at least once every few months. But is Oliver Tree really retiring this time?

Distractify spoke exclusively with him and learned what's next, if anything, and we tried to weed through the less serious parts of his persona that have made him such a sensation to millions.

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Oliver is serious about his singing career, but he's always quick to put on a show for anyone willing to listen. Half of the time, he's open about his career and his music, and the other half of the time he's "in character," so to speak, almost like Sacha Baron Cohen's Ali G persona.

The result is that fans are constantly wondering how sincere Oliver is about literally everything, but they eat it up all the same.

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Is Oliver Tree actually retiring?

Oliver often threatens to retire or insists that his album or tour at any given time is his last. And when we asked if he plans to announce another retirement any time soon, he confirmed that the follow-up to the "Cowboy Tears" album, "Cowboy Tears: Drown The World in a Swimming Pool of Sorrow," will be "the last body of work" he releases.

Do we believe that? Not really. But Oliver had a number of reasons why he's allegedly (but likely not really) leaving the music business.

"It's looking like that's probably going to be the end of the line for me," he said of the deluxe version of the "Cowboy Tears" album. "I've been working on screenplays. And as you may or may not know, I'm partnering with Planters Peanuts, [so] right now I'm kind of getting into the food industry. And they just released this new flavor of Sweet & Spicy Peanuts… And so I just had my team kind of reach out and say, 'Hey, Oliver's a big fan of this product, and he's getting out of music.'"

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Oliver's claim of moving into the food industry is in reference to his partnership with Planters Peanuts and a DIY mullet wig fans can purchase for $4.49 starting on Aug. 12. They’ll also get a 16-ounce jar of Planters Sweet & Spicy Peanuts with it.

But something tells us that Oliver isn't really retiring from music, just like the handful of other times he has made the faux announcement.

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Oliver Tree has some new music in the works after "Cowboy Tears."

One reason we are inclined to doubt that Oliver is actually retiring this time is that "Cowboy Tears: Drown The World in a Swimming Pool of Sorrow" is on the way. The second part of the "Cowboy Tears" album features music with more of a pop-punk flair that Travis Barker helped Oliver create.

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The inspiration behind "Cowboy Tears" may surprise some fans.

Although "Cowboy Tears" isn't really a country album, it does have some country influence, and that's because Oliver comes from a long line of cowboys. He shared with us that his grandfather was a cowboy and that his great-great-grandfather was too.

And, during the COVID-19 pandemic, Oliver stayed at his grandparents' ranch and was inspired to write "Cowboy Tears."

"When I had retired for the first time, officially, I went back to my grandparents' ranch, and I was living there and I soaked up some inspiration," Oliver said. "I wasn't intending to release the album, but I just made some music there with this acoustic guitar. And I just fell in love with the sound."

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The result is an album that was a solid follow-up to 2020's "Ugly Is Beautiful."

Let's hope that, for the sake of his fans, Oliver continues to be inspired to make music and doesn't actually "retire" any time soon.

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