How a Berklee student went viral getting Bostonians to let their guard down

Alden McWayne, who goes by guicci_pineapple on TikTok, has gone viral for his videos complimenting Bostonians. (Jacob Garcia/WBUR)
Alden McWayne, who goes by guicci_pineapple on TikTok, has gone viral for his videos complimenting Bostonians. (Jacob Garcia/WBUR)

It’s a warm Tuesday afternoon and Alden McWayne, 21 years old and hard to miss with his shaggy mullet and thick mustache, has been wandering around Brookline for the past two hours looking for strangers to compliment.

“Nice mustache,” he tells one passerby. The man laughs and replies, “You too.”

Later, McWayne spies a woman in a bright overcoat waiting outside the Arcadian Hotel. “Red is your color,” he calls to her, eliciting a big smile. “You’re swagged out.”

Alden McWayne compliments Nancy Korman on her red coat. (Jacob Garcia/WBUR)
Alden McWayne compliments Nancy Korman on her red coat. (Jacob Garcia/WBUR)

He’s recording each interaction as inconspicuously as possible to later put up on TikTok where he goes by the handle gucci_pineapple. Less than 24 hours later, the video has racked up a million views and hundreds of thousands of likes.

McWayne isn’t new to this, a previously recorded compliment session downtown garnered over four million views. Back then, he was surprised that it got so much attention having filmed the material on a whim. “Turns out people love the gassing up,” he says.

It’s a simple formula that’s only successful because of the enigmatic personality behind it. In each clip, McWayne is unapologetically himself, and his unique confidence while approaching complete strangers is as much a draw as the grins that he brings forth with his compliments.


Over the last few years, he’s carved out a niche living among Bostonians. He’s noticed they often have “a hard chocolate shell, like on an ice cream cone,” that is readily penetrated by a nice compliment. “So many people have their guard up,” he says. “But if you can get it down, you realize they just want to chat.” And that’s proven true in his videos, but McWayne might be downplaying his own role in that. Not just anyone can take down a New Englander’s guard so quickly.

His older brother, Dana McWayne, says it’s how their mother raised them. “She raised us to not have a fear of the world,” he says. “To see the best in every single person you see on the street and know that they all have a story. Alden sees the world through those eyes and as a result, everywhere he goes, people love him.”

Users stumbling across Alden’s viral videos end up sticking around for his personality. His account has around 500,000 followers and they’re regularly treated to a wide variety of content. One day, McWayne will post an absurdist sketch, like the one where he and a friend wrestle when he finds out the coffee he’s drinking doesn’t meet his criteria (locally brewed, fair-trade and organic). “Bro really tussled with me,” he remembers. “I think I got a concussion that day.”



The next, McWayne is disrupting what looks like an actual college course to tell the camera, “I don’t think bro has a hall pass,” as someone leaves the classroom. After a person behind the camera reminds McWayne they’re in college you can hear a seemingly confused professor asking if he missed something.

Another day, he’ll invite viewers into the other of his two passions—music. In his final semester studying the drums at Berklee, McWayne is making a serious stab at being a musician. He and his brother, a saxophone player, release music under the name Dana and Alden and have a new album on the way. McWayne’s TikTok page is littered with live performances of various pop and hip-hop covers recorded with a rotating cast of friends and family in bedrooms, Berklee practice spaces and basements.

But it wasn’t always like that. McWayne says posting his music on TikTok felt risky three years ago. He’d originally started the page in his hometown bedroom in Eugene, Oregon to blow off steam during the pandemic lockdowns, and the content was exclusively comedic. He worried that the small fanbase he’d begun to cultivate might turn on him if he didn’t stay in his lane.

That isn’t McWayne’s way though. Comedy may have earned him some attention, but his music is an equally important part of him. Luckily, the people he had drawn into his world were down with his drumming reveal–a quick clip of him covering Thundercat’s “Them Changes” alone.


Encouraged, he returned to Berklee when the school reopened in 2021, continuing to post his combination of low-budget sketches, man-on-the-street interactions, and live music clips. His network at Berklee grew, and more musicians joined him to play covers, including his brother Dana who currently lives in South Carolina. Three years older, Dana says he didn’t quite get Alden’s online presence at first. The two were raised “off the grid” on flip phones, and social media wasn’t a big part of their lives. But now he says he’s Alden’s biggest fan. “I wake up every morning and check if he’s made a new video,” he laughs.

And Dana recognizes the power of his brother’s online following and what it can do for their music. At one point, Alden’s cover of another Thundercat track, “Dragonball Durag,” reached the feed of popular online music critic Anthony Fantano who tweeted it out. McWayne, grinning at the memory, says he woke up to a flood of texts from his friends about the repost and ran around his room screaming. The two have since struck up a friendship, and Fantano has even appeared on his channel.

McWayne has successfully turned this platform into one that boosts his lush covers and original tracks, but they continue to live in harmony alongside his goofy characters and skits. From Dana’s perspective, both genres spring from the same creative well within Alden that feed each other.


It’s probably for that reason that Alden lists two videos when you ask which of his TikToks is his favorite: One musical, the cover of Earl Sweatshirt’s “Riot!” The other comedy, a pun about overalls. It’s likely his devoted followers from around the country feel the same way and aren’t turned off by the whiplash combination of content on his page. You can even see some of the gucci_pineapple character come through in the way that McWayne gently plays the drums.

Now on the cusp of graduating from Berklee, and with that following and his supportive brother behind him, McWayne is looking toward expanding his horizons and booking shows to support the new album when it arrives. “It’s the album that we’ve always wanted to make,” he says. He’s even considering spreading his wings and making a move to New York City.

No matter what he does, you can count on him to do it the unadulterated McWayne way and to continue getting the genuine smiles that only he can elicit.


Headshot of Lukas Harnisch

Lukas Harnisch Contributor
Lukas Harnisch is a contributor to WBUR's arts and culture coverage.



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