It’s hard to imagine a time when Westside Gunn was a relative unknown in the rap game, considering the Griselda empire has evolved into a household name. In reality, Gunn has been steadily grinding since the early two-thousands, before plying his trade in the Buffalo underground circuit with his long-running Hitler Wears Hermes mixtape series. Between his own output and that of his brother Conway, who was also honing his own skillset, their discography was quickly building — as was their reputation as artists on the rise.

In March of 2017, it was announced that Westside Gunn and Conway would be joining Shady Records, with Eminem  praising the duo in an official statement. “The style and energy of Griselda Records, Gunn and Conway are infectious,” praised Em. “We can’t wait to put them on the platform they have earned and deserve.” The news came as somewhat of a surprise, as Gunn and Conway marked the label’s first signings since the assembling of Shady 2.0, a lineup that included Slaughterhouse and Yelawolf. Curious fans immediately began diving into both West and Conway’s extensive back catalogs, with many experiencing their first brush with the grimy and established Griselda sound.

Scott Dudelson/Getty Images

A few days after the big news, Westside Gunn, Conway, and Benny The Butcher sat down with Sway Calloway for an extensive conversation. The excitement was palpable. Westside Gunn seemed particularly thrilled by the partnership, revealing that Paul Rosenberg played a pivotal role in facilitating the process. As Gunn explains, he was initially looking to be represented by Rosenberg’s Goliath Management. “Paul was like ‘you know what, fuck the management, I got something better for ya’ll,” reflects Gunn. “I wasn’t even expecting it, cause I was working hard for a few years to make it happen.”

It’s likely that Gunn’s 2016 album Flygod played a role in cementing the Buffalo rapper as one to watch. Not to mention the mutual friends bridging the gap. Goliath Management artist Danny Brown held it down with a Flygod guest appearance, and Gunn had already established a working relationship with Em’s DJ — the legendary Alchemist. In any case, the future seemed bright. “I went and got the biggest bottle of Remy they had at the liquor store,” laughs Conway, in the same Sway interview. “El Camino rolled us a couple of celebratory things and we did it that way.”

Over three years have passed since the signing of Westside Gunn and Conway. Much has changed in the interim. Both rappers are pretty much stars, respected across the game and critically acclaimed with every release. Alongside Benny The Butcher, who did not sign with Em’s label (he claims he was still “rapping locally” at the time), they released their first Shady Records album in 2019’s What Would Chinegun Do, which featured the crew’s first collaboration with Eminem. At the end of August, Westside Gunn delivered his first official Shady Records album Who Made The Sunshine. Conway’s anticipated Shady drop God Don’t Make Mistakes is still awaiting release. Musically, the crew’s stock has never been higher. Yet every now and then, there appears to be slight friction between Westside Gunn and Shady Records, with the main issue seeming to stem from the promotional side of things.

That’s not to paint a wholly negative picture, as there have been many harmonious instances between Westside Gunn and Shady Records. Speaking with HNHH in April of 2018, Gunn described the process of working with the label as dope. “Eminem was always Conway’s favorite rapper,” explains Gunn. “He literally knows all of his projects. You can put him on the spot, he can rhyme the rhyme. He’s an Eminem fan. It’s really a dream come true for him — you get drafted to the Bulls after Jordan being your favorite player ever. Marshall has always been dope to me. I was always the Nas, Rae, Ghost, Prodigy, the street raw shit. But I always respected Marshall for the bars. That lyrically, he was one of the best. I can never take that away from him…It’s dope man, they supporting everything we got going on. Big up to the Shady staff.”

In that same month, Gunn elaborated on his own personal dynamic with Em during an interview with REVOLT TV. “Every time we see each other, he leaves with a smile,” reflects West. “I leave with a smile. We’re not together all the time. He has his life, I have mine. We’re grown men… I respect people and when I see you, I’ll see you.”

In October of 2017, not far removed from the signing of Compton rapper Boogie, Eminem’s newfangled Shady Records roster stepped up to spit some bars in the BET Digital Cypher, a clip that has since gone on to garner well over a million views on YouTube. Conway also landed his first Eminem collaboration with “Bang,” a cut originally recorded for his Shady Records debut. While the affiliation helped raise awareness for the Griselda trifecta, it wasn’t without a few jarring setbacks. For one, the influx of Stans, which ultimately led to Conway openly voicing his frustration. “They’re a bunch of nerds and Stans that don’t understand me or relate to what I bring to the table,” explained Conway, noting that many only appeared interested in Eminem.

Though some opted to interpret his words as disrespectful, Conway made it abundantly clear that it was all love between him and Slim Shady. “Me and my big bro Eminem got that “BANG” produced by Daringer and Beat Butcha available everywhere now!” he captioned, alongside a triumphant pic of him, Alchemist, and Eminem. “We got more shit in store for y’all too!!” In hindsight, it’s likely he was referring to What Would Chinegun Do, the 2019 Griselda album released courtesy of Shady and Interscope. The acclaimed project featured a remix of “Bang” with Westside Gunn and Benny The Butcher, as well as a rare verse from 50 Cent, fueling the Shady vibes with his presence. In spite of the album’s success, however, its post-release handling appeared to be the catalyst for some unexpected negativity, exposing some wrinkles in the seemingly harmonious partnership.

In June of 2020, when Griselda was nominated for a BET thanks to their work on What Would Chinegun Do, Westside Gunn took a moment to call out Shady Records for perceived negligence. “I wonder do @ShadyRecords know we’re nominated for a BET AWARD tonight,” he wrote, tagging the label in a challenging show of dominance. Gunn’s tweet swiftly made headlines, sparking a narrative that Griselda was growing unhappy with Shady Records, or at the very least, disappointed. Luckily, that didn’t hamper the release of Gunn’s Shady debut Who Made The Sunshine, which landed at the beginning of October. This time, the Shady Records Instagram page made a point of spotlighting the project, reserving plenty of space to promote Gunn’s experimental effort. But Eminem himself did not use his own personal page to promote the album, a fact not lost on the ever-watchful Westside Gunn.

After one of Em’s followers called out the rapper for neglecting to promote Westside Gunn’s Who Made The Sunshine — on a post celebrating The Alchemist’s The Food Villain — Gunn himself seemed particularly amused by the situation. He proceeded to pen a telling response, his emojis speaking volumes: three crying-laughter emojis followed by three “shhhh” emojis. Clearly, he has a few issues with the way Shady Records — and Eminem, for that matter — have been promoting Griselda, an entity that has made plenty of waves on their own merit. It’s difficult to get a sense of Gunn’s expectations of the partnership, as the majority of his commentary has been made on social media; conversely, neither Eminem nor Paul Rosenberg has appeared particularly fazed on the Shady end.

At this rate, one has to wonder what will happen after the release of Conway’s own Shady Records debut God Don’t Make Mistakes, an album that has been widely touted as one of the year’s most anticipated drops. It should be interesting to see the promotional rollout that ensues, and whether it appears to satisfy Westside Gunn’s criteria for approval. Either way, regardless of where you stand on the partnership, it’s hard to argue that the Griselda/Shady era has culminated in some truly incredible music, and should be celebrated accordingly. While all is said and done, we’re looking at a run that gave us What Would Chinegun Do, Who Made The Sunshine, and soon to be God Don’t Make Mistakes. All things considered, that’s enough to leave a positive impression overall, no matter what the future holds.

What do you think of the Griselda and Shady Records partnership? Was Em’s label ultimately a good fit for Westside Gunn and Conway The Machine? And lastly, are you satisfied with the music that has come of it so far?