Justin Bieber Made Music With Disney Channel Star Kyle Massey

Once upon a time, Justin Bieber was a teen heartthrob who charmed audiences as a child, and later, as a teenager. Now, of course, he’s a married man, but longtime fans remember him as a child star. Bieber has a few child star friends himself, including That’s So Raven actor Kyle Massey.

Justin Bieber poses during a new studio photo shoot August 2020 in Los Angeles
Justin Bieber | Mike Rosenthal/Getty Images

Justin Bieber’s longtime friendship with Kyle Massey

Bieber’s friendship with Massey dates back nearly a decade and has been mostly documented on Massey’s social media. Massey’s relationship with the “Boyfriend” singer has been documented as far back as 2014 when he appeared in the music video for “Playtime,” a collaboration between Bieber and Canadian rapper Khalil.

In September 2019, Massey shared photos on Instagram of Bieber and his entourage at a studio. “Love you @justinbieber,” the caption read. “New album is out of this world!!!” The album Massey was referring to was Bieber’s platinum-selling 2020 album Changes.

Justin Bieber looking off camera in front of a blurred background
Canadian singer Justin Bieber on the red carpet | Axelle/Bauer-Griffin/Getty Images

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Kyle Massey makes music with his brother Christopher Massey

Many people don’t know that Massey himself is a musician. He performs with his brother, fellow child actor Christopher Massey, as the duo The Massey Boys.

Massey spoke about his music career and his relationship with Bieber in an appearance on The Real. “Big shoutout to Justin; he’s been a great friend of mine for a long time,” the Cory in the House star said. He credited Bieber and his brother, whom he said “showed [him] how to do music and take it seriously.”

The Massey Boys’ debut album is slated for release this summer, but Massey’s first priority for the coming weeks and months is promoting his new series Millennials.

Kyle Massey
Actor Kyle Massey arrives at Wells Fargo’s West Coast Screening of “A Raisin In The Sun” held at the AMC Magic Johnson Theater on February 11, 2008 in Los Angeles, California | Neilson Barnard/Getty Images

Justin Bieber and Kyle Massey recorded music together

It turns out that Bieber and Massey’s friendly relationship extends beyond just supporting each other’s projects. In a series of videos posted to Massey’s Instagram Stories when he was in the studio with Bieber that day listening to the Changes album, fans can hear snippets of unreleased music — including a song with both Bieber and Massey.

The song, presumably titled “Drew House” in reference to Bieber’s middle name, has never seen the light of day. But it might speak to Bieber’s hip-hop and R&B leanings in recent years. The lyrics are lighthearted, and the song was likely never meant to be anything more than two friends having fun in the studio over a hip-hop beat.

“Yellow and gold, let’s go Drew / It’s on the hottest brand in the world right now,” Massey raps. Bieber’s verse is simple as he raps about a girl “coming through” repeatedly. In videos of the listening session at the studio, Bieber can be seen enjoying the music, though it’s clear from his facial expressions that he doesn’t fancy himself hip-hop next biggest rapper.