Backseat Freestyle

By Jayson Rodriguez

Hip-Hop Award Season 2021



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Backseat Freestyle
Hip-Hop Award Season 2021
By Jayson Rodriguez • Issue #30 • View online
Welcome to Backseat Freestyle. This is my weekly hip-hop newsletter I send out every Friday (I know, I know, it’s Monday. See the editorial note below.) focusing on one big thing that happened over the past seven days. I also include links to what I’ve been listening to, reading and watching. You can check out the archives, here, and read more about me, here. If you’re already a B.F. subscriber, thank you for your continued support. Please share this newsletter with your circle so that they can enjoy it, too. If you’re arriving to this issue by way of a forward, LinkedIn or social media, please subscribe below. With that said, let’s get into it….
Editor’s Note: Backseat Freestyle hasn’t published in a while and I’m sorry for my absence. And tardiness. It’s a labor of love I enjoy and appreciate the conversation that emanates on social. But I got jammed up dealing with a photo rights claim and launching The Bridge: 50 Years of Hip Hop podcast. So I missed a week here and there; next thing I know a few months passed. I’m gonna drop this year-end recap and be back January 14 with a sequel to the 2021 predictions post. Then back weekly, unless noted. Buckle up!

Tyler, The Creator // Credit: Luis Panch Perez (Columbia)
Tyler, The Creator // Credit: Luis Panch Perez (Columbia)
Front Seat
This is what’s driving hip-hop this week….
The year 2021 in hip-hop proved to be stabilizing, in an unexpected way. Without major tours and with another year of activity limited by the pandemic, artist either put out material or risked sitting out another 365 until we could all go back outside fr fr. Who knows when that’s actually gonna happen? As a result we saw releases from a slew of acts across the spectrum of rap: newcomers, grey beards, lyrical wizards, mumble monsters, superstars and blue collared indies. It made for the most balanced year in recent memory.
With such a compelling selection of music to pick from for Year-End/Best Of lists, Backseat Freestyle is gonna trot out picks for MVP, Rookie of the Year, 6th Man and Most Improved. It’s a nod to the Al Lindstrom TV video series I participated in with Combat Jack, Joe La Puma, B.Dott, Jeff Sledge and (sometimes) Charlamagne. Given the continued evolution of consumption and the matter of cultural worth of an album vs. streaming hit; let alone, “projects,” the retail collections that are somewhere above a mixtape on the totem pole but not quite an album (maybe an artistic merit, maybe a cheap affix to hedge against poor sales), this activity always makes for an exciting debate. Without further ado, these are my picks for who was in the driver’s seat.
Back Seat
Respect my mind or die from lead shower.
Tyler, The Creator (Winner)
Lil Baby
Tyler the Creator Performs ‘LUMBERJACK’ at the BET Awards 2021
Tyler the Creator Performs ‘LUMBERJACK’ at the BET Awards 2021
Drake did Drake numbers and dominated the DSP landscape with Certified Lover Boy (read my CLB review over at and last year’s MVP, Lil Baby, was the most streamed artist on RapCaviar, cementing his elite status with such a strong year despite being off cycle. Meanwhile, Jadakiss (Looking At Jadakiss’ Legacy Outside Of Top 5 Debates) was surgical during his Verzuz appearance for the second year in a row and used showmanship and catalog to push himself into the conversation, a rarity. Had I dropped this newsletter in mid-December like I initially planned, Nas wouldn’t have even made this list (Maybe Lil Nas X? See: Get Off Lil Nas X’s D!ck. Maybe Doja Cat?) but his twin offerings, KDII and late arrival, Magic, were a reminder of the potency in his second (or is it third?) act.
It’s Tyler, The Creator, however, who I’m crowning the Most Valuable Player. The Off Future founder’s Call Me If You Get Lost is 2021’s best rap album (it’s not even close) and it’s such a strong showcase for his indomitable talents. His last two collections, 2017’s Flower Boy and 2019’s Igor, one critically acclaimed and the other a Grammy Winner for Best Rap album despite a lack of rapping, track much of what he’s talking about and even doing on CMIYGL. But his DJ Drama-fronted set is a Trojan Horse of an album, combining the merits of his previous work strategically designed to be more digestible with its cocksure boasts—yet underneath it all, is a love story that’s laced with themes of upward mobility, sexual identity and a redemptive arc from our prickly protagonist. It’s the entire Tyler experience of the past 10 years, brilliantly compacted in 52 minutes and 50 seconds. In an era where we relegate album supremacy to Kendrick Lamar or underground stalwarts, Call Me If You Get Lost’s success on a mainstream level is notable and a notch in Tyler Baudelaire’s designer belt. Cheers.
Pooh Shiesty (Winner)
Baby Keem
Nardo Wick
Pooh Shiesty - Back In Blood (feat. Lil Durk) [Official Music Video]
Pooh Shiesty - Back In Blood (feat. Lil Durk) [Official Music Video]
Baby Keem gets the headlines (and Grammy nod) because of his family ties and EST Gee has the output with his Bigger Than Life or Death + deluxe release. While Morray and Nardo Wick both have strong narratives to pair with strong music. It’s just so hard to steer away from Pooh Shiesty and his Shiesty Season mixtape. That it dropped so early in the year (February) and that the Memphis rapper has been jailed since early July, has stalled momentum that otherwise would have made this a runaway nod. It’s been a strong year for new jacks but none are as fully formed, with a mix of dark humor, bone-chilling flow and strong songs as Pooh Shiesty.
6th MAN
Latto (Winner)
Coi Leray 
Maxo Kream
Latto Freestyles Over Yung LA’s “Ain’t I” - L.A. Leakers Freestyle #123
Latto Freestyles Over Yung LA’s “Ain’t I” - L.A. Leakers Freestyle #123
This category was always a head-scratcher back in the day when we did this as a panel, but I took it to mean the person who was poised to level up the following year. Last year I tapped Lil Durk after his turn on Drake’s “Laugh Now Cry Later.” This year, following that same formula, the pick would be Gunna after he played Ghosface to Young Thug’s Raekwon on YSL’s Slime Language 2. It’s just that Big Latto’s been slowly building up in 2021 after her breakout in 2020. The obvious tell is “Big Energy,” a number one at rhythmic radio. That was the shot. It was the chaser that really set the table. Her freestyle on LA Leakers was a standout among strong contenders and rivals her XXL Freshman cypher. She’s ready, word to Tiffany Haddish.
Mach-Hommy (Winner)
Polo G
Lil Yachty
Key Glock
Doja Cat
Mach-Hommy - Folie Á Deux ft. Westside Gunn, Keisha Plum (Official Video)
Mach-Hommy - Folie Á Deux ft. Westside Gunn, Keisha Plum (Official Video)
A longtime maxim used by coaches is that the best ability is availability. For Mach-Hommy, who peddled his early albums direct-to-consumer via Instagram and other websites (Bandcamp, etc.), his releasing two albums for wide consumption on DSPs was a revelation. His Griselda offering, Pray For Haiti, was among 2021’s best projects and by year-end he upped the ante with Balens Cho (the better of the two, in my opinion.)
He’s always been a talented artist with a perspective that’s without many a peer. By making his two-part musical ode to Haiti available to the masses, the New Jersey wordsmith kept his core ideology in tact while a larger swath of fans re-position him in the conversation among today’s top talents.
Music, reads, podcasts and videos (music and more) I’m checking for. [Here, instead, I’m gonna play Chris Paul and drop 10 dimes on my favs of the past year.]
  1. Lil Wayne‘s feature run. For my money, his “Seeing Green” verse was the verse of the year. Apologies to Andre 3K.
  2. Dreamville’s rollout for J.Cole’s The Off-Season. Seamless.
  3. Whatever is going on with Flo Milli’s late year IG posts. She was in my top three for 6th (Wo)Man last year. Still bullish on her but I was a year early by the looks of her late '21 level up.
  4. Folarin II. Wale’s recent LP might be the one I revisited the most in 2021.
  5. Myke TowersLyke Mike album. Bars. Also, not sure why it wasn’t Like Myke.
  6. Benny The Butcher‘s moves. He’s who I tune into Griselda for, with all due respect to Westside Gunn and Conway The Machine.
  7. “Industry Baby.” Hardest line of the year might have been Lil Nas X’s “you wasn’t really rooting for me anyway.” The defiance in this track and video is the stuff of rap dreams.
  8. NBA YoungBoy’s fortitude. Doesn’t try to be what he’s not and his fans appreciate him for who he is.
  9. Ms. Lauryn Hill’s verse on Nas’ “Nobody.” L-Boogie knows all the tricks from Bricks to Kingston. So it shouldn’t be a surprise she seared this 16 but damn it felt good to hear her rap again.
  10. Give this brother his flowers, damnit. N.O.R.E. had another stellar year with “Drink Champs” and a run of guests that made for great headlines and trending topics (Kanye got all the ink but the Big Sean episode was top notch). He and DJ EFN are the top podders in the game. (Related: The Power Behind N.O.R.E.‘s “Yo, Do You Remember…”)
Backseat Freestyle is written and produced by Jayson Rodriguez for Smarty Art Media. If you have any comments, feedback or questions, feel free to email me: If you would like to discuss sponsoring an issue of the newsletter, contact: holler@ And follow me elsewhere:
(I added a couple of new links below recently because I might experiment with promoting Backseat Freestyle on TikTok or Twitch.)
Instagram: @jaysonrodriguez
Clubhouse: @jaysonrodriguez
YouTube: smartyartllc
Podcast: coming soon
Disclosure: I’m employed by Spotify’s Studio 4 and given that I frequently include public news and streaming numbers from Spotify in the newsletter, I want to note that the views and opinion reflected in Backseat Freestyle are solely my own. Also, as the showrunner of Nas’ podcast, The Bridge, I work with closely him, however, any inclusion of his music is without influence. —JR.
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Jayson Rodriguez

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