Today marks the 25th anniversary of the death of Christopher Wallace, the groundbreaking MC known as The Notorious B.I.G., Biggie Smalls, Frank White and, for many, the greatest rapper of all time. While his music and story remain extremely popular years later — drop “Hypnotize” at a party today and watch the crowd go wild — there are still details of Biggie’s career and legacy that most of his fans don’t know. As we reflect on Biggie’s legacy, here are five lesser-known facts about the late Brooklyn rapper.

1. Biggie was commanding crowds as a teenager.

Amazingly, Wallace was only 25 years old when he was gunned down in a crime that remains officially unsolved. Yet, Biggie was able to establish an unparalleled legacy in his few short years. By the time he became a commercial hit with his 1994 debut album Ready to Die, Biggie had already honed his skills through years of rapping in his hometown of Brooklyn. One of the earliest recordings of Biggie is a recording of a 17-year-old Wallace mesmerizing a crowd on a street corner.

2. Biggie was a commercial rapper — literally.

Though Biggie’s hardcore raps may not seem like the most likely fit for corporate branding, the MC’s commercial appeal translated into several commercials recorded by Biggie. Wallace spits advertising verses for both St. Ides malt liquor and Pepsi Cola.

Though most rappers would simply phone in such advertisements, Biggie absolutely kills it on both tracks.

3. Biggie and Pac freestyled together, and Spike Lee caught it on video.

Though Biggie and Tupac Shakur are remembered for their bitter feud, the two legendary MCs were friends before their falling out. Biggie and 2Pac recorded a few songs together, though most of these recordings were never officially released while the two MCs were still alive. However, perhaps the most obscure performance featuring Biggie and Pac is not a formal song. Rather, it’s a video of them freestyling together as they hung out. Shot around 1992 or 1993, the video is a nice throwback to the days before their feud split the hip-hop community. The lyrics are gritty and NSFW, but they also represent a rare informal collaboration from two of the greatest MCs to pick up a mic. Even more incredible, the footage was seemingly shot by Spike Lee; you can hear a voice that sounds like Lee coming from off-screen and 2Pac name-drops the director in his freestyle.

4. He was one of the few rappers to release a song with Michael Jackson.

The King of New York and the King of Pop collaborating somehow has not been remembered as the big deal that it was. Michael Jackson has a long history with hip-hop; his records and voice have been sampled on several songs, including Biggie’s own “Unbelievable.” Jackson was a big hip-hop fan. He recorded several collaborations with rap stars, though many of them ended up being unreleased for a variety of reasons. Biggie, however, has the distinction of being perhaps the only rap star to have not one but two official collaborations with Jackson. Biggie dropped a verse on the 1995 song “This Time Around, a track from Jackson’s album HIStory: Past, Present and Future, Book I.

Six years later, Biggie was posthumously included on Jackson’s final album, Invincible. The album’s opening track, “Unbreakable,” features a Biggie verse borrowed from Shaquille O’Neil’s song “You Can’t Stop the Reign.”

5. His children are continuing his legacy.

Biggie left behind two children: daughter T’yanna Wallace, who he famously shouts out as his “baby girl” in the song “Juicy,” and son Christopher Wallace, Jr. with singer Faith Evans. Though both T’yanna and Christopher were very young when they lost their father, they have carried on their dad’s legacy.

T’yanna now operates a Brooklyn clothing boutique named Notoriouss in honor of her father. Among other things, she releases a special t-shirt on March 9 to commemorate her dad’s death. T’yanna has other business ventures as well; last year, she collaborated with the late Jam Master Jay’s daughter Tyra Myricks to open a New York-style pizza restaurant in Los Angeles. The restaurant is named Juicy. Meanwhile, Christopher Jr., known as C.J. Wallace, is also an entrepreneur; he co-founded the cannabis company Think BIG in 2019. Beyond his business ventures, C.J. has shown the same charisma as his father and has also entered the entertainment world. C.J. has acted in several movies as well as the TV adaptation of the Scream horror franchise. Appropriately, his very first role was playing the child version of his dad in the 2009 Biggie biopic Notorious.

Twenty-five years after his death, the legacy of the Notorious B.I.G. live son in his music, his impact on the world of hip-hop and his children.