Pepsi's Biggie Ad Is OK, But These Videos of Him Freestyling Are Incredible

We did a little digging and found some killer, 90s-era footage of The Notorious B.I.G. freestyling about things other than a soda company.
Drew Schwartz
Brooklyn, United States
October 26, 2020, 4:30pm
Biggie Smalls and Tupac
Screengrab via YouTube

Pepsi has described its latest ad campaign, which features a previously unreleased Biggie Smalls freestyle, as a way to "celebrate" the legendary Brooklyn rapper's legacy—and, of course, to celebrate Pepsi. In a press release, the soda company touted Biggie's verse as a token of his “unwavering love [?] for ice-cold Pepsi," recorded off-the-cuff during an interview on New York's Hot 97 in 1997.

Watching the ad, you might think that Biggie's freestyle came out of nowhere, a random product of his allegedly deep devotion to the company's Refreshing, Delicious Beverage™. In reality, according to Biggie's friend DJ Enuff—who was there when Biggie recorded it—this verse was always meant to be an ad.

"To be honest with you, there was another rap group that we saw put down a commercial for a competing soda company and we were excited about that," DJ Enuff told OkayPlayer. "The fact that [Biggie] wanted to do one, I was humbled, like, 'Let’s do it.' So we came up with a funny concept, me just searching the fridge and just [trying to] find something to drink, and I find him a Pepsi. I throw it to him and he just starts rapping about the Pepsi, and that’s as simple as it was."

DJ Enuff told OkayPlayer he's been trying to get a Pepsi ad featuring the freestyle made for years, but Voletta Wallace—Biggie's mother, who manages his estate—has always turned the offer down. When DJ Enuff and Pepsi pitched it to her as a celebration of Biggie's upcoming induction to the Rock 'n' Roll Hall of Fame, throwing in a contest through which one lucky rapper will ultimately get some free studio time, Wallace apparently agreed to it. Last Wednesday, she gave the ad her official sign-off on Instagram.

"Nothing can beat the P-E-P-S-I, yes I drink it constantly / Something ’bout the taste feels great, less filling" aren't Biggie's hardest bars, but hey—it's still nice to hear something new from one of the greatest rappers who ever lived.

This ad may not convince you to crack open an ice-cold Pepsi, but if it makes you want to go down an internet wormhole to find other Biggie freestyles from the 90s, you're in luck. We did a little digging and brought the wormhole to you, compiling some essential videos of Biggie freestyling about things decidedly less PG than a soda company. Here they are, presented in order from Very Badass to Unbelievably Badass, for your viewing pleasure.

Biggie's Freestyle on a Brooklyn Street Corner—1989

Biggie was just 17 when this footage was taken; it would be five years before he put out his first album, Ready to Die, on Bad Boy Records. It's difficult to say for sure, but this video appears to capture what's now become a legendary cypher, which—according to DJ 50 Grand, Biggie's former collaborator—happened on the corner of Bedford Avenue and Quincy Street in Bed- Stuy, Brooklyn, in 1989. Here's what DJ 50 told The Fader about that day:

People in the neighborhood knew him as the hottest rapper around. Everybody that stepped in his path, he ate 'em up. He earned that stripe from that one battle he had on Bedford and Quincy. I was the one that was playing the music. This man used to live right upstairs from the pool room. Every day in the summer we'd play the music out. It just so happened that Big came around, so we brought the grill out, we brought the music out. They got on the mic and went at it. It went on from there. Cars stopped, it got real crowded out there. We rocked it 'til 12, one o'clock that night. It was a good look. Everybody that came at his back, he took out.

Biggie's Freestyle on 'Teen Summit'—1992 (or 1993?)

This footage is from an episode of Teen Summit, a BET talk show that ran from 1989 to 2002. Biggie's performance aired in either 1992 or 1993; he would've been about 19 years old.

Biggie's Freestyle With Tupac—Sometime in the Early 90s

It's unclear when this footage of Biggie and Tupac freestyling together was taken, but it must have been filmed sometime between 1993, when the two of them first met, and November of 1994, when Tupac was shot at New York City's Quad Studios and accused Biggie of being involved, bringing an end to their short friendship. It appears to have been filmed by Spike Lee; you can hear him speaking to the two rappers in the beginning of this extended cut, and Tupac shouts him out partway through his verse. "And my other homies out here like Spike Lee," he raps, pointing at the camera, "they got the camera on a n***a guess they like me."

Biggie's Freestyle on 'The Wake Up Show'—1997

This footage was recorded during a segment of San Francisco's The Wake Up Show, with hosts Sway and DJ King Tech, in 1997. It's a testament to just how talented at freestyling Biggie was, a prime example of his ability to rap off the top of his head pretty much endlessly. But that wasn't just a skill of Biggie's; according to his former manager, Wayne Barrow, that was all he ever did.

"The first time I was in the studio with him I realized he didn't write," Barrow told The Fader in 2011. "I'd never seen anyone do that before. It amazed the heck out of me. At that point I'd be in the studio with some of the greatest artists, but I've never seen no one on either side of the spectrum—whether it be the R&B side or the hip-hop side—be able to create the type of songs that he created from his mind. No pen, no pad. Getting in the booth and just laying it down in damn near one take.
"

Follow Drew Schwartz on Twitter.