Following the release of his hip-hop-heavy Believe, MTV News looks at the young pop star’s swaggiest moments.

You’d think a 1995 collaboration between the King of Pop, Michael Jackson and rap’s widely recognized G.O.A.T., the Notorious B.I.G., would have made a bigger wave, but when MJ released “This Time Around” with Biggie Smalls 17 years ago, mixing pop with hip-hop was still very taboo. Despite the top billing, the track hit with a relative thud. The truth is it just didn’t feel organic, it’s not like Mike grew up listening to rap in Gary, Indiana, in the 1960s, the art form as we know it today just didn’t exist.

Justin Bieber was a 1-year old when the King of Pop snagged the King of Hip-Hop for a feature. And unlike Jackson, he grew up during an era when rap stars like Biggie, Snoop Dogg and Tupac Shakur were just as big as their pop counterparts — sometimes bigger. That’s why Bieber mixes hip-hop so seamlessly on his new album Believe.

“One, I think they know it’s authentic and two, you got to remember Justin’s past,” JB’s manager Scooter Braun told MTV News. “I was the vice president of So So Def Records and then I left and Justin was the second artist I found after Asher Roth. So here’s this 13-year-old living in Atlanta, no one knows who he is, and he’s just riding around with me and we’re in the studio with Ludacris. We’re in the studio with T.I. We’re in the studio with Big Boi from OutKast, hanging out and he got exposed to that really early.”

Ludacris, Drake, Big Sean and Nicki Minaj all appear on the 13-track Believe, but JB’s hip-hop jones didn’t develop overnight. It’s been years in the making. MTV News takes a look back at seven of Justin’s defining hip-hop moments.

“Baby” featuring Ludacris
JB didn’t have much rapper swag when he dropped “Baby” with Ludacris at the top of 2010, but the track sounded good, especially when Luda dropped his rapid-fire bars over the feel-good track. When he performed a remixed version of the track with fellow Canadian Drake at the 2010 Juno Awards, Justin further proved that he can rock with rap’s finest.

“We Are the World 25 For Haiti”
After the devastating earthquake in Haiti in 2010, Quincy Jones assembled an all-star cast of musicians like Kanye West, Usher, Janet Jackson and Justin Bieber to remake the 1985 classic. During the recording, the Biebs got to kick it with notable MCs like Lil Wayne, Busta Rhymes and his long-time friend Nipsey Hussle.

The Swaggest GIFs Of Justin Bieber Ever!

“Runaway Love” Remix Featuring Kanye West and Raekwon
Justin Biebs proved he “ain’t nothing to f— with” in August 2010 when he linked up with Kanye West and Raekwon for his “Runaway Love” remix. The Chef and Yeezy rapped on the track which sampled Wu-Tang Clan’s dusty underground favorite “Wu-Tang Clan Ain’t Nuthing Ta F— Wit.”

JB and Nicki Sitting In A Tree
So what do Nas and Justin Bieber Have in common? OK, kissing Nicki Minaj on the cheek at the 2010 Video Music Awards doesn’t really give Justin that much rap cred, the voluptuous Nicki could sing country music and we would’ve been just as jealous.

“Speaking in Tongues” Freestyle
Let’s face it, if you plan on spitting rap bars, the name Justin Bieber just isn’t going to cut it. Enter Shawty Mane: JB’s swagged-out alter-ego. Back in October 2010, Justin showed that singing wasn’t his only talent when he rapped over Vado and Cam’ron’s “Speaking in Tongues.” The freestyles didn’t stop there; Shawty Mane also spit bars over the Throne’s “Otis,” Gang Starr’s “DWYCK” and the Notorious B.I.G.’s “Who Shot Ya?”

The Biebs Shuts Up Tyler, the Creator
It takes a lot to quiet Odd Future’s resident loud mouth Tyler, the Creator, but when he and JB met in February 2011, the multiplatinum pop star didn’t let Wolf Haley get a word in edge wise. “When I got in there, he was talkin’ about the ‘Yonkers’ video and sh–. It was weird, because I was sitting here starstruck, like, ‘Oh, f—, it’s Bieber. He’s asking me questions.’ I’m like, ‘Shut the f— up so I can talk to you,’ ” Tyler told MTV News.

Lil Swaggy Is Born
Not only did 2 Chainz bless JB with a killer verse for his “Girlfriend” remix, the ATL hit-maker also blessed Bieber with a new moniker. “I call him Lil Swaggy,” 2 Chainz told MTV News. Sounds like a winner to us.