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‘Billboard Unfiltered’: Wiz Khalifa’s Legacy, The Blog Era & Drake’s Versatility

Written by on March 5, 2025

Billboard Unfiltered returned on Wednesday (March 5) with another live episode, but the guys added a special guest into the mix — Hot 97’s DJ Drewski makes his debut on the newest iteration of the show.

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Wiz Khalifa’s recent run of fiery freestyles and features has the crew feeling nostalgic as they discussed Wiz possibly forcing his way back into the mainstream, which led to a debate surrounding The Blog Era.

“There is a commercial appetite for Wiz,” senior charts & data analyst Trevor Anderson said. “I would love to see Wiz get another hit … Just to cap off this era, how crazy would it be if there was a comeback single that made its way… If he was able to sneak back into a top 40, top 20 kind of hit, that, to me, would only solidify when you look at that 15-year run.”

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For deputy director, editorial Damien Scott, he appreciates that Wiz has found what fans love about him, and is continuing to fill the void.

“It’s good to see an artist realize what people love about them and understand there is something they could still give to the game,” Scott added. “Wiz sounds like he wants to rap again. He got so successful … I don’t think he has anything to prove, but he sounds reinvigorated and wants to prove to people that he can still do this.”

The fellas highlighted a Blog Era artist they’d like to see make a comeback: Damien Scott went with Charles Hamilton while Trevor Anderson highlighted B.o.B. Carl Lamarre went down to Atlanta for Ace Hood and Drewski chose Asher Roth.

Scott got another discussion going when recalling a viral tweet comparing Jay-Z, Nas and The Notorious B.I.G. as the best lyricists. “I would go with Biggie as a lyricist,” Scott said. “I think Big had everything. I think he had every aspect of rap. Big was so nasty, I don’t think rap has dramatically moved on from what he’s done.”

Lamarre chimed in with a spicy take when claiming that “from a dexterity level,” J. Cole could go “toe-to-toe” with Biggie and hold his own on a track. “I think he could go toe-to-toe with a Jay,” he said. “Especially this new version of Cole we’re getting.”

Another heated discussion came off of the theory of Drake being planted in the ’90s and seeing how much success he’d have with his singing-rapping hallmark in the Golden Era. Drewski believes Drake would’ve thrived on a Bad Boy Records under Diddy’s tutelage, while Damien Scott isn’t so confident.

Scott thinks Drake owes a series of thank-yous to Kanye West for paving the way and breaking down sonic barriers in the years prior to his ascension. “The change that took place because of Kanye, Drake benefitted from greatly,” he said. “Back then, that s–t wasn’t flying.”

Watch the full episode below:

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