“He could make you laugh. He could make you think”: How Biggie Smalls became a rap legend

At 24 years old I remember driving around with a suspended license, drinking too much alcohol, never eating vegetables, smacking a guy with a Hennessy bottle for a reason I can’t remember, and having my cell phone turned off every month because I always forgot to pay the bill. And I was considered to be the “responsible friend.” I was wild, reckless, and extremely content with making bad decisions every single day. I could not dream of the reality that I enjoy now almost 20 years later and remain extremely grateful that I got a chance to grow up. 

By 24, rapper Christopher Wallace better known by his stage name The Notorious B.I.G. was already one of the most talented rappers in the history of the art form – selling millions of records, touring the world, being nominated for multiple Grammys, winning a Billboard Music Award, Soul Train Music Awards, Source Awards and more. He had everything figured out, escaped poverty and was a master of his art from before his brain was fully developed – a true genius. Gun violence cut the rapper’s life short; as a result we will never know what he could have been. This year, the year Biggie would have turned 50, Justin Tinsley, sports and culture reporter for ESPN’s Andscape, formerly The Undefeated, takes a deep dive into the life of Christopher Wallace and the powerful legacy he created in such a short time in his book “It Was All a Dream: Biggie and the World That Made Him.” 

Tinsley – who is most known for beautifully crafted 1990s nostalgia-filled takes, ESPN’s “Around the Horn” appearances and his ESPN 30 for 30 Podcast, “The King of Crenshaw,” which explores the legacy of the late rapper and entrepreneur Nipsey Hussle’s brotherhood with some of the premiere players in the NBA – talked to me about his connection to Biggie Smalls and what this book will mean historically for the world of rap and culture. 

You can watch my “Salon Talks” episode with Justin Tinsley here or read a Q&A of our conversation below to hear more about the difficult but rewarding time he had compiling stories for the book. 

The following conversation has been lightly edited for length and clarity.

“It Was All a Dream” took me down memory lane. Why did you decide to put out a book on Biggie right now?

I always wanted to write a book. Everything I knew about the book publishing industry dictated that I come up with an idea and I pitch it and then the publisher decides whether they want to move forward or not. My experience was different. Around fall of 2019, I’m just going through my emails and I’m just deleting spam, and I come across one that says, “Biggie book?” I come to find out, it was a gentleman who eventually became my editor on the book, his name is Jamison Stoltz and he works at Abrams Books. He was like, “Yo, you come highly recommended from some people I know, and I’m looking to commission a biography of Biggie Smalls that’ll come out in May 2022 in conjunction with what would’ve been his 50th birthday.” The book was researched, reported, and largely written during quarantine. It gave me a lot of time. I couldn’t go anywhere. I was in the Google doc damn near 24 hours a day.

One of the things I was thinking about when I was reading the book was how so many younger people who are going to pick up this book may not have even heard of Biggie. Take us back to that era and the cultural relevance of Biggie.

When we talk about hip-hop, when you mentioned the ’90s, especially people who were around to live it and experience the music, you mention ’90s hip-hop and 9.9 times out of 10, you’re going to get a big smile that come across people’s faces. People will say like, “I was this age when this album came out. I’ll never forget where I was when Dr. Dre’s ‘The Chronic’ came out or Snoop Dog’s ‘Doggy Style,'” or whatever the case may be. The ’90s was the era where the critical artistic value of the genre ran parallel with the commercial explosion of it. 

It’s largely thought to be spearheaded by the West Coast and what Death Row [Records] was doing. They changed the game. Then shortly thereafter, Puffy created Bad Boy under Arista and he had Craig Mack. People forget, before Biggie became Biggie, the first superstar on Bad Boy was Craig Mack. You couldn’t go anywhere without hearing “Flavor in Ya Ear.” 

It was a great time, musically, but also you can’t talk about the highs without talking about the dark lows. And obviously, the two darkest moments of ’90s rap would be the murders of Biggie and Tupac. And of course, also losing Eazy-E in 1995, due to the AIDS virus. It was such a turbulent, traumatic in a lot of ways, but such an artistically beautiful era of music that really shaped a lot of people’s artistic palate for what they liked in rap, for what they grew up on, and how they still connect with the genre even now. We’re talking about Biggie Smalls, it’s been over a quarter century since he passed. It’s crazy, man.

I think the way that you cover culture, especially the 1990s, is brilliant. I always learn something new from your essays. I feel like you might be one of the only people I know to ever write about “Above the Rim.”

I’m glad you mentioned “Above the Rim” because running parallel with the music was the movies and the TV shows. We talk about “Martin.” We talk about “Fresh Prince.” So many classic shows were coming on during the ’90s that it

“You’re always going to be partial to the music that really defined the most impressionable parts of your life.”

created this ecosystem of Black culture that is really hard to duplicate. And I don’t think it has been duplicated in the 30-plus years since. 

When I was coming up, the older guys didn’t want to hear about Nas. They just wanted to talk about Rakim. Do you think we get biased about music because of the eras that we grow up in?

I always told myself I’m never going to be one of those “Get off my lawn”-type of dudes because I have little cousins and they tell me about the artists that they’re rocking with. And whether or not I really rock with their favorite artists or not, I always try to give them space and grace because I remember when people, older heads were telling me, like, “Oh, Jay-Z ain’t that nice. He’s cool, but he ain’t LL. He ain’t Rakim. Outkast ain’t Run DMC,” or something like that. 

You’re always going to be partial to the music that really defined the most impressionable parts of your life. We’re going to be the same way. I try to give space to the younger generations and give them their moment because at some point they’re going to be the old heads, too. And there’s going to be some other music out there, like “Lil Uzi Vert was my favorite artist.” I get it, man. 

I also think it’s very important, too, in hip-hop, as competitive as it naturally is, it’s important to have these times where we pay homage to these artists, like the Jay-Zs and the Bigs and the Nas-es, because without them, hip-hop wouldn’t be where it is right now. There’s a way to do that without knocking the current generation, but I’m still finding my footing on all that, as well.

Take us back to the first Biggie song you ever heard.

I love this question. So, I want to say the first song that I remember hearing is my older cousins were playing “Party & Bullshit.” I do remember that, but I didn’t really know who Big was at that point because at that point that was really the only song he had that was resonating outside of New York, and the Mary J. remix, of course. 

“There was a person in Christopher Wallace with hopes, dreams, insecurities and flaws.”

I remember hearing “Juicy” for the first time in the summer of ’94 and I just remember listening to it with my mom in the car. She didn’t really know what it was, but she recognized the sample. She’s like, “Oh, man. I know this song.” She was like, “Who is this?” I was like, “Mom, that’s Biggie Smalls.” And she was like, “Who is Biggie Smalls?” And obviously, she quickly came to know who he was. I would say “Juicy” would probably be the first time that I remember hearing it and I knew it was a special song. I was only nine or 10 years old at the time, so I couldn’t really understand the significance of what that song actually meant. I was calling myself ashy to classy, but I didn’t really know what it meant. You know what I mean? It sounded cool. So that would be my first one. 

My most hilarious memory with Big was when my uncle, who – God rest the dead; he passed in 1999 from colon cancer – but that dude is the reason, to this day, I love “Martin” so much. He watched every episode of “Martin.” I’ll never forget watching the episode of “Martin” where Big was on there. If I close my eyes, I can still see myself in the living room of my uncle’s studio apartment in DC, and he’s just like, “Oh, man. Biggie Smalls is on this episode.” He was like, “I like Big.” And he was like, “Biggie Smalls is so cool.” Keep in mind, my uncle is almost 20 years older than this dude at this point, like, “This is a cool young brother right here.” And I’m thinking, my uncle is the coolest guy in the world. So, if he thinks Big is the coolest guy in the world, then I got to love the guy.

It’s crazy because, even though Martin was in the industry in Hollywood, it felt like Biggie was bigger than the actual show. Did you feel that way?

In my research for the book, I read some backstories on that episode. Martin would always be super playful when they weren’t filming, always cracking jokes, making everybody feel comfortable, but people were like, “Yo, that time when Biggie came on, Martin was on his best behavior because he was like, ‘I want to make sure Big has a lot of fun doing this. I’m a big fan of him.'” And obviously, Big was a huge fan of Martin Lawrence, as well, so the admiration was mutual. But yeah, looking back on that show, and even when you watch it now in 2022, when he first says, “Still cracking jokes, ain’t you?” and then he walks out and you hear the crowd go crazy, you can see Martin’s face and he’s like, “Damn, I got Biggie Smalls on my show.” This is Biggie Smalls in 1995, the biggest rapper in the world. It did feel like he was bigger than the show at that point, which sounds crazy to say because we know how culturally relevant, historically relevant the show “Martin” is.

“The first album came out in September 1994.

He was gone by March of 1997.”

I was on the basketball court that was across the street from a bunch of houses. It had to be 30 or 40 of us on the basketball court. And my homie, Nate, he came to the window and he’s like, “Yo, Biggie got shot.” Then the whole basketball court is around this little TV, watching Kurt Loder on MTV or something like that. We’re watching it and everybody was just broke. That’s one of the moments that will stick with me for the rest of my life. What was you like when you got that news?

Just hearing you tell that story, man, I got goosebumps. That’s one of those life moments that you’ll never forget where you were, and you’ll never forget that feeling in the pit of your stomach. He got shot on an early Sunday morning. So, we were going to church the next day, my mom, my grandma, my brother and I. They were telling me, “Go to sleep early so you don’t fall asleep in church.” I did not go to sleep early. It was 3:30 in the morning because Big got shot shortly after midnight in LA, so it was 3:30 back over here. And I’m just watching MTV and, out of nowhere, it just says, “Breaking News, the Notorious B.I.G. shot and killed in a drive-by shooting in Los Angeles.” I’m like, “What?” The school year started off with Tupac getting killed and then, in March, Big was dead. I just remember thinking, this can’t be what it is. Even at that age, I was 11 years old, I’m like, “Yo, this can’t be what rap is. This can’t be the future of my favorite artists.”  

When they got shot, Pac and Big, I thought, that’s super tragic that they died. I’m very sad about that, but at least they got to life a long life. They got to be 25 and 24 years old. I’m thinking, “They lived a long life.” That ain’t nothing. In the research for the book, I was just talking with psychologists, as well, and they were like, “Your brain isn’t even fully formed until you’re 26 or 27 years old. You’re still learning things about yourself.” 

My mom was a single parent and she knew Big grew up with just his mom and she was like, “Yo, my heart goes out to his mother because I wouldn’t know what to do if my only child . . .” I just remember my mom was really sad. She didn’t really understand the complexities of everything going on at the time, but she didn’t need to. She just knew, somewhere out there, another mother was grieving the death of her son. And she knew Tupac’s mom had done that a couple of months earlier.

I remember going back to school that next Monday and everybody was just talking, like, “I don’t know what this is going to be,” and just talking with people within the industry at that point in time, like Danyel Smith and Elliot Wilson, two really good friends of mine now, they told me straight up, it was like, “Yo, this is it. Rap is over.” 

Many people had been predicting rap’s downfall, like, “Oh, this is a genre, it’s a trend. It’ll eventually die out, like disco did, and this is it.” And a lot of people felt like it. We just lost the two biggest names that we’ve ever had in this genre within six months of each other, like “This is it. It has to be it. I guess I got to find another career now.” Thankfully, that wasn’t the case, but those are moments that we’ll never forget. Especially if you’re deeply embedded in this culture and you grow up in it and you have a genuine love for it. We’ve moved on, but those are wounds that’ll never heal, never, never heal.

What are some things that you learned about Biggie while writing this book?

For one, when he was younger his favorite genre of music was country because his mother played it in the house all the time. And to his friends at elementary school, he would be like, “Yeah, I can’t go to sleep at night without my country music.” And all his friends were like, “Country music?” His mother was his first DJ, in a sense. She moved from Jamaica to New York and she loved country music growing up in Jamaica, so she brought that to Brooklyn with her. And obviously, her child was influenced by that. 

“Women wanted to be with him. Men wanted to be like him.”

Another thing, I always knew fatherhood was important to him, but I learned just how important it was. A lot of people don’t expect to hear suburban soccer dad when it comes to Biggie Smalls, but that was his dream in life. He wanted to make enough money in music to where he could just kick back and, “T’yanna want to do this. I want to take her there. CJ want to do this; I’m going to always be there. I’m going to be at the school plays. I’m going to be at the football or the basketball games. I’m going to be front [row] and center. I may have messed up in some of the romantic relationships in my life, but now that I have these two young people who depend on me and who need me, I want to be there because I didn’t have that growing up.” Up until the day that he passed, he was saying to friends, “I can’t wait to get back to New York so I can see T’yanna, so I can see CJ. I want to take them to the park. I just want to be in my kids’ lives.”

We hear about Biggie Smalls all the time, but there was a person in Christopher Wallace with hopes, and dreams, and insecurities, and flaws. That’s what I really wanted to do with this book. Obviously, we know about his musical career. We understand the high points of that, but I wanted to peel back the layers and show that he was still a young man trying to figure life out. He was 24 when he died. I know I ain’t have life figured out at 24.

You write about his death at the end of the book. What do you think justice looks like for him? Because we know all the parties involved. One person is dead, one person is locked up forever, and then there’s the other person who’s lingering.

I know there’s several conspiracy theories out there about what actually happened. I tend to subscribe to Greg Kading’s research and his investigation. I do believe it looks like what Greg Kading’s said. I won’t give away the entire quote, but the party that is still around, that is not dead or incarcerated, I believe that that person owes Ms. Wallace and that family, “This is my role, and this is what happened,” because again, you can’t bring him back. We understand that, but Ms. Wallace deserves that. His kids deserve that. There is power in accountability, even if it is a quarter century later. 

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The ’90s are backc—cthe music, the fashion, the TV reboots. What do you think it was about Big that made him the god of that era?

For one, the music was fire. Of course, the music was dope, but the music was dope because it just basically played into who he was as a person. When you saw Big, if you didn’t know anything about Big, and he walked in the room, you would see this big, 6’3″ or 6’4″, 300-pound Black guy with shades. He looked imposing, he looked menacing, he looked like everything that you would think a stereotype about a person like him would be. But the moment he started engaging with somebody, he disengaged you from the moment. 

Women wanted to be with him. Men wanted to be like him. The music was fire, and his personality was so engaging and he could make you laugh, he could make you think. You wanted to hang around this guy for all those reasons. And then he dressed fly. He put Coogi on the map. You can’t say the word Coogi without thinking about Biggie. And then, of course, once he got his money up even more, he was wearing Versace. He was a style icon. 

“Heartthrob never, Black and ugly as ever,” he played on that. He was like, “Look, I know I don’t look like Tyson Beckford. I know I don’t look like Denzel, but dammit, I’m a sex symbol, too.” He had an unwavering type of confidence that you couldn’t shake. We talked about the “Martin” episode and there wasn’t really anything couldn’t do, from a creative and influential and impactful standpoint. There’s never been an artist in history, not just rap history, but I’m talking musical history, there’s never been an artist who accomplished so much in such a short period of time as Biggie Smalls did. If you think about it, the first album came out in September 1994. He was gone by March of 1997. That’s two and a half years, basically, two and a half years to do everything that he did. And here it is 2022, and we’re still talking about him. 

We’ve all seen this meme. One’s got to go: Tupac, Biggie, Jay-Z, or Nas. First, you must boot a person off, but after you boot the person off, you have to rank the other three with little to no explanation.

You’re going to get me killed for this. All right, I’ll play along. Tupac, Biggie, Jay, Nas. You might hang up on me when I say it. I’m going to kick off Nas. Then put Jay at one, then Big and then Pac. 

Watch more “Salon Talks” on hip-hop with D. Watkins


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