Justin Timberlake’s Failure To Sign Justin Bieber To A Record Deal Cost Him $40 Million

Summary

• Timberlake lost out signing Bieber due to a bidding war launched by Usher.
• Usher leveraged his name against Timberlake to convince Bieber to choose Raymond-Braun Media Group over Tennman Records.
• Usher sold his share of Bieber's catalog for $40 million, in sharp contrast to Timberlake's ability to amass wealth from other ventures.

Justin Timberlake is one of the definitive pop stars of the 21st century. He managed to escape the boy band curse, became one of the most celebrated and sought-after musicians of the 2000s, and did it all while generating staggering album sales. Timberlake's music career is a success by any metric, except one: signing new talent.

Like so many established musicians, Timberlake tried to put his experience to good use by starting a record label and locating the next big star. He got close to making good on his plans by signing Justin Bieber, but a bidding war ruined Timberlake's chances, and he lost out on an eye-watering $40 million as a result.

In this article, we will highlight the deal that almost came to be, why it fell through, and how it benefited one of Timberlake's professional peers.

Justin Timberlake Engaged In a Bidding War To Sign Justin Bieber In The 2000s

Justin Timberlake was at the peak of his powers in the mid-2000s. His sophomore album, FutureSex/LoveSounds (2006), sold four million copies and spawned a handful of top 10 singles. As a result, Timberlake was emboldened to start his own record label, Tennman Records, in 2007.

According to the official press release, Tennman Records would operate as a joint venture with Interscope Records, and Timberlake, who named the label after his home state of Tennessee, would serve as the label's Chairman and CEO. It was under these conditions that Timberlake tried to secure a deal with burgeoning pop star Justin Bieber in 2008.

These details came to light during a 2024 People Magazine profile with Usher. The R&B star revealed that he was involved in a bidding war with Timberlake, after spending years in direct competition for the inheritor of Michael Jackson's "King of Pop" crown:

We built a friendship... and it was a bit of a bidding war between me and Justin Timberlake."

Timberlake and Usher felt that Justin Bieber was the future of pop music, and noted that Bieber took influence from both of them. Bieber's 2008 cover of the Usher single "U Got It Bad" was one of his first viral videos on YouTube, and the year before, Bieber had taken a crack at Timberlake's hit "Cry Me A River."

Ultimately, Timberlake came up short. Bieber decided to pass on a deal with Tennman Records, and sign with Raymond-Braun Media Group (RBMG), which was launched in 2008 as a joint venture between Usher (last name Raymond) and talent manager Scooter Braun.

Bieber was the label's first signee, and the rest, as they say, is history.

Justin Timberlake's First Name Was The Reason That Justin Bieber Signed With Usher

While Timberlake has not spoken publicly about his desire to sign Justin Bieber to a record contract, Usher was quick to recount the specific reasons that Bieber signed with him instead. In Usher's estimation, Bieber would always be forced to take a backseat to Timberlake because of the similar music they make and the fact that they share a first name: Justin.

Usher told People Magazine that he hammered this point home when trying to convince Bieber to join Raymond-Braun Media Group, and felt that it played a huge role in the young star's ultimate decision. He recounted his sales pitch succinctly:

"So if you want to go with Justin, that's Justin and Justin. Me, it's only one Justin. So that obviously created a relationship."

There was validity to Usher's point. From the moment Bieber established himself as a viable pop star, fans have been quick to pit him against Timberlake under the pretext of determining the best "Justin." Usher, meanwhile, believed that there were just enough similarities and differences between him and Bieber for them to both excel.

Reflecting on Bieber's decision, Usher claimed that it was the smarter move because it gave the young pop star time to figure out who he was as a performer and a persona, instead of immediately being compared to the biggest "Justin" on the planet:

"I think that he was trying to find himself as well... [I told him] 'I'm going to give you my passion, and every bit of what I have to offer."

It's hard to question the results. Bieber's first release under RBMG, My World 2.0 (2010), sold 4 million copies, and he has since gone on to surpass Timberlake and match Usher when it comes to worldwide album sales.

Usher Was Able To Sell His Share Of Justin Bieber's Catalog For $40 Million In 2022

Justin Timberlake has done exceedingly well for himself in the decade and a half since the Justin Bieber deal fell through, but it stands to reason that the former would be significantly wealthier if he had been able to win the "Baby" singer over.

While it would have been tough to quantify how much money Bieber has made for his mentor, Usher, and therefore determine how much Timberlake would have made in his place, Usher's decision to sell his portion of Bieber's publishing in 2022 made it easy. Usher was able to sell off part of Bieber's publishing for $40 million, according to Billboard.

That's a nice chunk of change regardless of net worth. To Timberlake's credit, he has still been able to amass a larger net worth than Usher thanks to his endorsement deals and acting roles in blockbuster films like Shrek The Third (2007) and Friends With Benefits (2011).

Here's how the net worths of these dueling pop titans stack up in 2024:

Despite becoming competitive over the signing of Justin Bieber, Usher maintains that he has no ill will towards Justin Timberlake, and credits him with being a source of inspiration during the 2000s.

Usher went as far as to tell People Magazine that he would be open to making music with Timberlake at some point in the future, and that his legacy is something to be proud of:

"I think that he has a legacy that should be respected. He should be recognized for who he is."

Fingers crossed that we eventually get said collaboration.