Joshua Goldman
Joshua Goldman
min read · August 15, 2025 · Entertainment

Justin Bieber's Night Out with Controversial Star: Fans React

Justin Bieber indulged in a night on the town this week with his controversial friend, former Disney Channel child star Kyle Massey

Justin Bieber's Wild Night Out with Controversial Pal Kyle Massey Raises Eyebrows

The spotlight is shining bright on Justin Bieber once again, this time for his scandalous night out with his close friend and fellow troublemaker, former Disney Channel star Kyle Massey. The Biebs' health concerns have been ongoing in recent months, with fans worrying about his gaunt appearance and hollow eyes. But it seems like Justin is letting loose and having the time of his life!

On Wednesday, the pop superstar took to Instagram to share a glimpse into his wild night out at the West Hollywood nightclub Zouk. The album included an intimate photo of him cozied up close to Kyle, with the latter hiding behind one of his arms. Talk about a code-red for discretion! But we all know how much Justin loves the drama – and so does Kyle, it seems.

In Justin's new Instagram album about the Zouk party, he also posted a video taken of a crowd of revelers on the dance floor including him and Kyle

Kyle Massey, 33, rose to fame as the adorable little brother Cory Baxter on That's So Raven back in the day. However, he hit headlines four years ago when allegations surfaced that he had been sending explicit images to a 13-year-old girl! Yeah, you read that right – a grown man trying to pass himself off as some kind of predator. In his defense, Kyle vehemently denied all allegations and claimed he was the real victim.

But here's the juicy part: despite these allegations against him, Justin Bieber is still BFFs with Kyle. The two have been inseparable since 2015, when their mutual friend Lil Twist got busted for breaking into Kyle's apartment (yes, you read that right – breaking in!) and robbing his brother Chris. That was a whole can of worms, but the real kicker comes from July 2021: Kyle faced a felony charge for "immoral communication with a minor" after allegedly sending explicit material to a 13-year-old girl!

Now, don't get us wrong; everyone deserves second chances and a chance to clear their name. But when you're in the public eye, it's hard not to raise an eyebrow (or two) whenever your friend gets accused of such serious allegations. Not to mention the civil lawsuit filed against Kyle back in 2019 – which claimed he was involved in some kind of predatory pattern with several young women!

Massey played Corey Baxter on That's So Raven - pictured 2003

Meanwhile, while Justin was out getting his party on with Kyle at Zouk, his wife Hailey Bieber was living her best life just a stone's throw away at Alba restaurant. She was joined by an A-list entourage featuring Kylie Jenner, Kendall Jenner, Bella Hadid, and transgender model Alex Consani! Now, that's what we call a girls' night out!

Justin has been addressing their marital issues on his new album, Swag – but the real question is: can their relationship withstand all these drama-filled friendships? The Biebs have maintained a united front so far, with Justin posting a series of loved-up photos and videos showcasing their snuggles and picnic blankets. But can we really trust that everything's hunky-dory in paradise?

After all, as the old saying goes: "The friends you keep..." We're keeping our fingers crossed for Hailey and Justin – but also giving Kyle Massey a serious side-eye from now on!

In July 2021 Massey was charged with a felony for immoral communication with a minor over allegations he sent pornographic material to a 13-year-old girl - he denied all the allegations - pictured 2021