The True Story of Diddy and Justin Bieber Explained

The True Story of Diddy and Justin Bieber Explained

Welcome to WatchMojo, and today we’re exploring the history between Sean ‘Diddy’ Combs and Justin Bieber.

Part One: The Lost 48. Hrs.

Diddy - or Puff Daddy - was already an established performer and music mogul by the time Justin Bieber was born on March 1, 1994. That same year, Diddy welcomed another young protégé to Puffy Flavor Camp. Usher was a young teenager when he went to live with Diddy in New York for a year. Diddy executive produced Usher’s debut studio album and introduced the rising star to his excessive lifestyle. Reflecting on Diddy’s “wild” parties in 2016, Usher said he’d never send his children to Flavor Camp. That didn’t stop one of Usher’s protégés from working and partying alongside Puffy. After Scooter Braun discovered Justin Bieber on YouTube, the 13-year-old singer met Usher. Braun and Usher founded RBMG Records, delivering a launching pad for Bieber’s career.

Although Usher provided a common link, Bieber directly contacted Diddy through Twitter on October 15, 2009, asking if he’d collaborate on a song. Diddy quickly responded, “send me the song. Ill check it out. Thanks.” Bieber soon found himself at Diddy’s house with a few others. Although they didn’t record a song, the two shot a video where Diddy promised Bieber a Lamborghini for his upcoming 16th birthday and a mansion for his 18th. Addressing the camera, Diddy said Bieber would be with him for 48 hours. This video saw a resurgence in 2024 as Diddy faced charges of abuse and sex trafficking. These accusations left people viewing the video in a much different light, prompting them to question what happened over those 48 hours.

While there isn’t a detailed record, the fan wiki Bieberpedia has potentially connected a few dots. The video was posted to Bieber’s YouTube channel on November 9, 2009. According to Bieberpedia, though, the video was shot on October 31. That same day, Bieber recorded a bit for 97.1 AMP Radio and modeled for the clothing company Levi’s. By nightfall, Bieber was trick-or-treating with his friends. Diddy notably isn’t present in any of these photos. On November 1, Bieber tweeted that he couldn’t travel to Vancouver for a show as planned because of an illness. If Bieberpedia is accurate, it’s possible that Diddy wasn’t actually with Bieber for 48 straight hours and that video was more of a publicity stunt.

Another video posted to Diddy’s YouTube page on December 15, 2010, also garnered concern amid his recent arrest. When Diddy asked why they hadn’t hung out for a while, Bieber gave him a fake 555 number. Knowing what we know now, some have interpreted this as Bieber trying to distance himself from Diddy. This seems unlikely for three reasons. 1) If that was the case, Bieber probably wouldn’t have shot the video or accepted Diddy’s “Dirty Money” swag. 2) Bieber obviously wasn’t gonna give his real number in a public video. 3) Diddy and Bieber were seen together several times throughout the following years. Most notably, Jimmy Kimmel interviewed them in 2011 where Diddy said Bieber “knows better” than to share what they do together.

Part Two: Stuck With U

Bieber started to gain a “bad boy” reputation after being arrested in January 2014. Pulled over for suspicions of drunk driving, Bieber was also accused of drag race, driving with an expired license, and resisting arrest. Diddy defended Bieber, saying he would ensure the young artist made more responsible decisions. This wasn’t reflected behind the scenes. A month after his arrest, Bieber was seen at one of Diddy’s parties in Atlanta. Rick Ross, Lil Scrappy, T.I., and several others were also in attendance. Bieber was still a month away from turning 20. Although the media focused on Bieber’s behavior, few questioned the nature of Diddy’s parties or why so many adults were partying with someone who hadn’t even turned 21 yet.

Bieber attended Justin Combs’ 21st birthday in 2015. Then when Bieber turned 21, he recorded a video with Diddy. Drinking tequila together, Diddy claimed that this was Bieber’s “first shot ever.” For Bieber’s 22nd birthday, Diddy presented him with a Bad Boy letterman jacket. By early 2020, it appeared Bieber had committed to getting his act together, expressing a desire to start a family with his wife Hailey. In an Apple Music interview, Bieber also tearfully made a vague statement about wanting to “protect” Billie Eilish from the industry hurdles he endured as an up-and-coming artist. Bieber didn’t name any names and could’ve been alluding to any number of struggles. Through a modern lens, though, it’s hard not to think of Diddy.

A few months after the Apple interview, two Twitter users accused Bieber of sexual assault. Bieber denied these accusations and filed a defamation suit against the users, which he later dropped. Bieber weathered through this scandal with the media’s attention soon shifting to Diddy. In 2021, Diddy was recorded checking to see if Bieber was wearing a wire, albeit playfully. In 2023, Bieber was featured in the song “Moments” for Diddy’s fifth studio album, “The Love Album: Off the Grid.” Over a decade after Bieber reached out to Diddy on Twitter, the two had finally collaborated on a song. “The Love Album” was possibly the last high point of Diddy’s career. It also might’ve marked the end of his friendship with Bieber.

Part Three: Monster

In November 2023, Diddy’s ex Cassie Ventura filed a lawsuit against him, alleging assault and sex trafficking. Despite settling, Diddy lost in the court of public opinion after footage of him seemingly beating Ventura was leaked. More lawsuits piled up before Diddy’s arrest in September 2024. After Diddy’s indictment, over 100 others (some minors) would join in legal action against him. While Diddy has denied these claims and is innocent until proven guilty, the public may never view him the same way again. As such, the photos of him hanging out with Bieber have taken on a more disturbing sentiment. Given Bieber’s age at the time and the crimes that allegedly took place at Diddy’s parties, some have questioned if the young artist was groomed.

Around the same time as Diddy’s arrest, Bieber seemingly released a song about losing himself at a Diddy party. The song includes unsettling lyrics like, “I was in it for a new Ferrari, but it cost me way more than my soul.” According to researchers, though, this viral song is almost certainly AI-generated. As of writing, the real Bieber has remained mostly silent about his former mentor. About a month before Diddy’s arrest, Justin and Hailey Bieber welcomed their first child. As Diddy dominated headlines, a source said that Bieber just wanted “to focus on being a great dad and husband.” A source also claimed that Bieber was “advised to stay as far away as possible from anything and everything related to Diddy.”

Supposedly, Bieber is “completely disgusted” by the accusations against Diddy and wants “nothing to do” with him. While Bieber is reportedly having a hard time processing his history with the fallen music mogul, “his happiness being a dad has outweighed his anxiety about Diddy.” Much remains unclear about Bieber’s time with Diddy and many of these questions may ultimately go unanswered. Online sleuths will surely continue to read between the lines, but for now, speculation is all we have to go on. It seems two things are for certain, however. Diddy was once somebody that Bieber looked up to. Now, not so much. What once seemed like a fifteen-year-old’s dream has become a nightmare for everyone involved.

What’s your take on Diddy and Bieber? Let us know in the comments.