Welcome to the 62nd issue of Backseat Freestyle. This is my weekly hip-hop newsletter I send out every Friday(ish) featuring a deep dive analysis on one big thing that happened over the past seven days. I also include a roundup of links to what I’ve been listening to, reading and watching. You can check out the archive, here, and read more about me, here. If you’re already a BF subscriber, thank you for your continued support. If you’re arriving to this issue by way of a forward, LinkedIn or social media, please subscribe below. And please share this newsletter with your circle so that they can enjoy it; personal referrals go a long way toward my goals for growth. With that said, let’s get into it….

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This is what’s driving hip-hop this week….

THIS ONE IS A BIT MORE PERSONAL and, perhaps, as a result a touch less hip-hop. But if you want to get to the rap shhh right away, scroll down to the Trunk (Music) section for last week’s picks. I’m still basking in the Bad Bunny halftime performance. The song selections, the visuals, the representation. I’ve said if often in this newsletter: hip-hop as a whole, from artists to fans, should feel a stake in his success. He’s plenty influenced by the culture, even if he raps way less than he used to compared to the start of his career. Back then, during those early days, I saw something in him and it reminded me a lot of the same feeling I had when I first got into Big Pun and Beanie Sigel. This essay is a needle I’m trying to thread between the three, although I do think there’s a broad lesson at the core of this unlikely trio. About world building, speaking for the few but being a beacon for the many and putting your people on your back.

🚙 🚙 🚙 🚙

Respect my mind or die from lead shower.

BACK IN 2005, WHEN I WAS A MEMBER of the music team at Vibe (the group that was responsible for the Next section, music features and album reviews), during a regular meeting, we were going over the ratings for reviews that were set to run in the forthcoming issue. Granted, we weren’t The Source with its mics or XXL with its size ratings, but the idea of awarding the correct rating weighed heavily on us. So when I saw we were giving Beanie Sigel’s The B.Coming a 3.5 out of 5, I protested. The album was urgent and intense, underscoring the last days of Sigel’s freedom before he turned himself in for a stint in federal prison; “Feel It in the Air,” peeled back the levels of his paranoia; “Bread & Butter” found a young Sigs going toe-to-toe with Brand Nubian’s Grand Puba and Sadat X! By all accounts, it was an excellent, if slightly flawed, album (it lost steam over the last three or four tracks). Despite my feelings, my argument got shoved to the side and I was labeled a Philly homer. (I was born in Wilmington, Delaware; and grew up in the suburbs, just a 30 minute drive to South Philly.) For sure, Beans resonated with me differently because of locality; his accent and the blocks he named checked had a familiarity to them. It didn’t blind me, however. It made me see him more clearly. Instinctually, I understood what he represented and his authenticity. Coupled with his flow and bars, I knew he was a special talent from the moment I first saw him perform “What a Thug About” years ago at Power 99’s annual Powerhouse concert. Still, that B.Coming experience stung and I allowed it to stick with me too long like a bad hangover. 

While I couldn’t clearly articulate what I wanted to say about Sigel then, it wasn’t the first time I felt that way. In 1997, it struck me for the first time when I saw the video for The Beatnuts’ “Off the Books.” Big Pun kicked off that track with a scorcher of a verse that was lyrical in the fashion of the rap that I loved, but aggressive in the way that only MC’s from New York could be; plus, he had the swag of a guy who would appear at one of my extended family parties and I’d never quite know if he was actually related to me or not. I was immediately drawn to Pun. This was also around the same time I ventured up the New Jersey Turnpike to go to the Puerto Rican Day Parade for the first time. Although I wasn’t a Nuyorican, the combination of each culture felt so grounding as an identity. (The first time I visited New York I must have been around nine and I vowed to move there when I got older.) By the time I regularly visited the city in my late teens, Big Pun’s music was my personal soundtrack to those experiences. The slang, the Spanglish, how he braided his hair, the faces in his music videos it sounded like an echo and felt like looking in a mirror. 

Which brings me to Bad Bunny. When I started at MTV News, my partner in pen, Shaheem Reid, told me the role was intense and I’d need to find another activity to decompress. He’d go to the movies solo and shut off his phone. Or he would go to old school shows as a way to distance himself from his work covering that new. Ultimately, I started playing softball. But my relationship to music became so professional and tied to my occupation. I found solidarity in the comment I often heard ESPN hosts say: they were no longer fans of certain teams or specific players, they were instead fans of the entire sport. Although their rooting interests waned, they replaced it with a greater appreciation for the game. That’s how I feel about hip-hop. Young or vet? I’m into it. Lyrical or vibes? Press play. There was never a delineation for me like coastal or underground, it was simply is it good or is it bad. 

The first time I heard Bad Bunny, though, I became a fan again. I found a genre that was similar to what I loved yet there wasn’t an overlap: Latin Trap. And that was Bad Bunny at the start. He had that booming baritone and a rapid rat-tat-tat-tat delivery. He wasn’t as rugged as the Boricuas from Uptown or Brooklyn that I’d come to know. His body was all awkward angles as his lanky body bounced across the screen in his music videos and his face was cherubic, rounded like the shape of the moon. He reminded me of a light-skin version of my cousin, Oscar, who I would only see every few years as a kid when I visited Puerto Rico and we drove to my father’s hometown in Naguabo. 

At the time, Bad Bunny was un musico sucio. Early records like his feature on Becky G’s “Mayores” or “Chambea” highlight a young Benito threatening to either cock his D or cock a hammer. There was a little Big Pun in him mixed with some Trey Songz “Mr. Steal Your Girl.” He still has that reputation. Though, over the course of his career, as he’s toned down his tawdryness a touch (and his rapping), he’s managed to become more like a Marvin Gaye mixed with just a bit of Kendrick Lamar. It’s been a joy to witness. 

I’ve written about his musical journey before, so I won’t go too much into that evolution. But as he’s gone deeper into his roots on each subsequent album, what I’m most struck by is how he’s able to tell the story about the Puerto Rican diaspora and its history as colonized land and it feels like he’s telling your singular story. As his Super Bowl halftime show began, when the visual of the sugarcane fields appeared, I felt a swell of emotions. My paternal grandfather cut sugarcane (under exploitative conditions) and my father, as a child, was a runner, bringing anything that the elder men needed or running errands for the bosses in charge. The famous casita that Bad Bunny showcased during his Puerto Rico residency and was the center piece of his Super Bowl set bears a striking resemblance to my grandmother’s house (hers was white with teal trim). The jokes about Jessica Alba being there on the porch as a stand-in for the No sabo kids cracked me up. I was definitely that kid with my wela; trying my best to talk with her but my vocab was so limited I’d yield after a coupe minutes and tell her Yo no sé more often that I liked. 

Now, I’ve upgraded to conversational Spanglish levels. So when the strings to “Monaco” pierced through my television speakers and Bad Bunny spoke about believing in himself, I laughed when I heard him say the first lines of the song: “tell me, this is what you wanted?”–and the production cut to Lady Gaga singing in English. Ha! With the swell in my chest moving to my throat, it all got the best of me when Ricky Martin appeared. The sounds of Menudo often rang throughout my house growing up and Ricky Martin’s light only burned brighter over the years as he went from childhood singer to telenovela actor to adult star. 

The thing about getting older, especially when you have kids, is trying to reconcile things from your childhood with what you want your own family to represent. Having moved to New York then relocating to the suburbs (again, just 30 mins outside of the city), there’s less of my Rodriguez family around. The sounds and smells that were so common to me are less frequent for my daughter. There’s a part of her that I have to actively work to present versus the osmosis I was able to experience in my youth. In 2023, I took my parents, my brother and my daughter to Puerto Rico for a week and rented a house for us all to stay in. I had conversations with my father about his life before he moved to New York. I went to places my parents spent time together before they had kids. I hopefully created a memory my daughter will cherish long into adulthood. It meant even more to me when I recall a comment my father said to me as we drove through the countryside and saw the roads dotted by abandoned homes. He said so many in our culture were getting older on the island and not many young people were coming back to claim land that was theirs. My father isn’t a man of many words, so it was striking because he was speaking to the generational connectivity that keeps Puerto Rican lore alive. 

Enter the cuatro player, Ricky Martin sitting on the micro set that was a replica of the DeBÍ TiRAR MáS FOToS album cover. And that song, “Lo Que Le Pasó a Hawaii.” Martin only sang (passionately so) a portion of the chorus, which translates roughly to “Thеy want to take my river and also my beach/ They want my neighborhood and my grandma to leave/ No, don't let go of the flag nor forget the lelolai/ 'Cause I don't want them to do to you what happened to Hawaii.” It spoke so much to my childhood and my adulthood. Tears slowly began falling down my face. 

By the time Benito got into "El Apagón,” his song about the blackouts in the aftermath of hurricanes Irma and Maria, and the imagery of power lines, the sugarcane fields and him emerging carrying the flag with its original sky blue cover, I was in awe. It was such a powerful shot. There’s just things that you see and your gut instantly tells you all you need to know, because your life has calibrated you to render a judgement in an instant. That…is its own reward. Although, I’d be remiss if I didn’t say, the writer of that Beanie Sigel review told me looking back he should have given that album a four out of five. When you know, you know.

Music, news, reads, podcasts and videos that I’m checking for this week.

Last edition of BF, I wrote about J. Cole and all the expectations for The Fall-Off. It’s an abnormal album for a final project; I was surprised by the lack of a narrative on it. But, as always, there’s quality raps throughout. There’s also a lot of observations about today’s rap game (take a shot every time you hear the word algorithm). I have a theory: Cole releases another album later this year on the independent tip under his full government name: Jermaine Cole. [Listen]  Related: Cole’s Trunk Sale series. [Watch]

Central Cee untethered this freestyle from Drake’s Iceman stream. [Listen] Related: His next project, an EP, All Roads Lead Home, arrives March 19. 

The love songs from rappers ahead of Valentine’s Day peaked a few years ago, but Lady London makes sure she got her lovey dovey on via “Buy Me Something.”  [Listen] Related: Coi Leray and Justin Laboy talk about dating and all things love in this lovey dovey chat. [Watch]

A Boogie Wit da Hoodie returns with a standout EP, Before Artistry. How y’all feeling about the Bronx young gun? I think he has quality output (“Red Light” with Trippie Redd rings out) but he seems stuck in how the game view him.  [Listen]

Speaking of quality, this is a sound trio: Sexyy Redd, Key Glock and a Tay Keith beat power “Hang Wit a Bad Bitch.” [Listen]

The ever underappreciated Kenny Mason returns with what we used to call a maxi single courtesy of his three-tack EP,  Pup Pack: 3rd Shift. Check the Jodeci-sampling “Moonlight.”  [Listen]

Grammy-winning rapper Lefty Gunplay (never gonna get tired of typing that) reintroduces himself with “What’s My Name”  featuring JasonMartin (I might need to write about Problem’s rebrand soon).  [Listen]

Sickamore is Billboard’s executive of the week after Don Tolliver scores a number one album. [Info]

Jimmy Iovine had some interesting comments about streaming; though I understand his argument, I don’t see DSPs as the vehicle to be delivery what he says artist’s need. [Info]

It’s feeling like go-time for xaviersobased, he’s gracing the cover of The Fader and had a prime interview with The Kid Mero. [Read] [Watch] Related: Mero got prime treatment from RollingStone [Read] 

Memphis Bleek’s podcast has quietly become one of my favorites. The Cam’ron and Beanie Sigel interviews are standouts. But his latest, with Jaz-O, demands your attention. [Listen]

Another rapper turned podcast, T.I., has also become a good podder. I didn’t listen to the 1.0 version of expediTIously, but since he’s relaunched it it’s been on my radar. There’s not many better conversations you’ll hear than this one between Tip and DJ Toomp. [Listen]

There’s a crudeness that’s characteristic of NBA YoungBoy and Chief Keef’s work. That’s part of their Horatio Alger charm. But, man, Mike WiLL Made-It really super charges them with his production. I wasn’t so impressed by Mike WiLL’s reunion with Swae Lee but this one is a banger. The superproducer’s new album is due March 20th.  [Watch] 

I like Ryan Witherspoon a lot; he has a natural charisma and a voice that was born to rap. His breakout paid homage to Pun and French Montana. He’s back with “Take Money,” a Jadakiss collab. It’s solid but I want to see more consistency from the upstart. [Watch]

Speaking of consistency, Juvenile has been on a streak. His latest, “B.B.B.” finds the veteran rapper flexing. He’s doing veteran rap right.  [Watch] Related: Juvie’s Still 400 The Mannie and Juvie Show had a dope episode featuring T.I.  [Watch]

Baby Keem is back and he’s walking fans into his next project with a YouTube docuseries; it seems like a good way to elevate him beyond his familial ties to Kendrick. [Watch]

Backseat Freestyle is written and produced by me, Jayson Rodriguez, impartially and independently via my company, Smarty Art. If you have any comments, feedback or questions, feel free to email me: [email protected]. If you would like to discuss sponsoring an issue of the newsletter, contact: [email protected] and check out the rates, here. And follow me elsewhere:

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The results of the Hip-Hop Award 2025 poll were titled in favor of Malice and Pusha T. Though Carti and Cardi also got love. And Gregg Kaysen chimed in, in favor of JID: “Thought [he] had one of the best albums of the year.”