The phrase “time is of the essence” may bleed into all walks of life but it’s one that harbours a particular relevance in hip-hop. Defined by an unquenchable thirst for the next big thing, success in the rap game requires an innate ability to strike while the iron is hot and capitalize when your cultural significance reaches its peak. While some MC’s are lucky enough to become overnight sensations, other rappers take a while longer to find their feet and are left to toil in the doldrums, just waiting for their opportunity. Conversely, some artists opt to rebuff offers that come their way or patiently bide their time in the belief that what’s meant for them has yet to arrive.

From Missy Elliott being reductively saddled with claims that she was “too fat” to be successful to Jay-Z recalling how labels thought he was “terrible” prior to Reasonable Doubt, there are plenty of examples where icons had to endure hardship in order to secure a deal from short-sighted record execs. On the other hand, there are occasions where artists-turned-CEOs passed on an artist that would go on to set the world alight, and underground sensations chose not to heed the call of the big leagues.

Tyler, The Creator & Rick Ross

Tyler, The Creator performing at Coachella 2018 - Kevin Winter/Getty Images

In recent times, this longstanding trope has reared its head in two case studies. For one, it recently emerged that Tyler, The Creator refused to even acknowledge Rick Ross’ advances on behalf of Maybach Music Group with a phone conversation. According to Diamond Supply’s Nick Diamond, this was endemic of a trend during Odd Future’s rise to prominence:

“Rick Ross called me out of nowhere and was like, 'Yo, what’s up with Odd Future? I wanna talk to that Tyler kid. I want to sign him. It was funny, ’cause when he called me, Tyler was actually in the store, standing next to me. So I was like, 'Rick Ross wants to talk to you.' Tyler goes, 'I don’t want to talk to Rick Ross.'”

2 Chainz & Jay-Z

2 Chainz and Jay-Z at the Roc Nation 2017 brunch - Ari Perilstein/Getty Images 

In the wake of his new album Rap Or Go To The League, 2 Chainz detailed how it was an issue of integrity and brotherhood that prevented him from signing with Jay-Z’s Roc Nation:

"The only reason that I did not go was because I said, 'Can I bring my buddy Tek with me?' He was like, 'Why you wanna bring your DJ for?' But I'm trying to tell them that bruh helped me get to the point where I'm on your radar, you know what I'm saying? I couldn't go by myself. I just chose loyalty."

Lil Wayne & Jay-Z

Lil Wayne at a World Series game 2018 - Ezra Shaw/Getty Images

Alongside his status as a GOAT contender, Jay-Z’s status as a music industry magnate has meant that he’s found himself on both sides of this double-edged sword. After speaking on his own ill-fated attempts to get a deal, Jay has tried to pave the way for new artists to come aboard Roc Nation and its Roc-A-Fellla predecessor with mixed results. In one particularly errant move, the tale of Hov’s attempts to sign Lil Wayne in 2005 taught him a lesson on the dangers of undervaluing an artist. As described to Streetz Is Watching Radio, Tunechi balked at a low bid from Jay at the 40/40 Club:

“That man offered me 175 [thousand dollars]...two teeth in my mouth is 175. My bottom teeth. So we laugh about that all the time.”

Joey Bada$$ & Jay-Z

Joey Bada$$ at TIDAL X: Brooklyn in 2017 - Theo Wargo/Getty Images

For fellow Brooklynite Joey Bada$$, his decision to abstain from taking the Roc Nation bag came from an anecdote from Jay-Z's Decoded: “There’s this one chapter where [Jay-Z] went to meet with Russell Simmons to sign with Def Jam. He said his only thought sitting across the table from Russell Simmons was ‘I don’t wanna be signed to this n***a, I wanna BE this n***a,’ I kinda had that same perspective.”

Drake & T.I.

Drake performing in Atlanta 2016 - Paras Griffin/Getty 

On a lesser scale, another man that’s felt the brunt of both sides is OVO Sound head honcho Drake. Before he morphed into one of commercial hip-hop’s biggest exports, he was just another burgeoning rapper on the industry ferris wheel. During his formative stages, Grand Hustle CEO T.I opted to leave Drake on the sidelines. Detailed to The Breakfast Club, Tip admits that he saw no longevity in the Six God’s signature ambiance:

“It was Drake before the beard. Bare-faced Drake, you know what I'm saying? It just hadn't caught all the way up yet. That type of music, that sound of music, the emo sound. It wasn't necessarily prevalent at the time. I didn't see the curve.”

When it came to assume the mantle of label founder, Drake saw his own hopes to sign two now prominent acts dashed when he got rebuffed by A Boogie Wit Da Hoodie and Bryson Tiller respectively.

J. Cole & Jim Jones

J. Cole performing at the NBA All-Star Game half-time 2019- Jeff Hahne/Getty Images

A self-professed comrade of Drake’s, Dreamville’s, J. Cole is no stranger to his own near-misses as both signer and signee. In an interview on ItsTheReal’s Waste Of Time podcast, Diplomat Records’ Jim Jones revealed that he once passed on the “Middle Child” of hip-hop. In terms of his reasoning, it came down to a basic lack of foresight as he stated that “J. Cole didn’t have a team when they came to me, He didn’t have a team, it was just J. Cole rapping.”

J. Cole & Kendrick Lamar

Kendrick Lamar at the 60th annual Grammys - Gareth Cattermole/Getty Images

Years before he’d rise to meteoric heights, a fresh-faced Cole also tried to acquire the services of Kendrick Lamar at the nascent days of Dreamville. During a chat with the late Combat Jack, Cole explained that he immediately saw a diamond in the rough:

“I actually wanted to sign him, but I didn’t have my business right. I didn’t know he was with Top. But in my mind, he was the first person I ever found. … I remember tellin’ everybody like, ‘Yo, I’m tryna sign this kid. Like yo, this ni**a’s nasty!”

Chance the Rapper, Danny Brown & TDE 

Chance the Rapper performing in Brooklyn, 2018 - Nicholas Hunt/Getty Images

In a more tragicomic tale, Joyner Lucas has described how he tried to attach himself to the Dreamville wagon only for Cole to allegedly ignore his text. Speaking of K-Dot, his spiritual home of TDE has had its own fair share of acquisitions that never materialized. In a case of wish fulfillment for hip-hop heads, ScHoolboy Q has intimated that they very nearly brought Danny Brown into their stable. Based off of collabs with him and Soul, Q wished to add the Bruiser Brigade general to Black Hippy and was “telling my homies to sign him.

Synonymous with independence, Chance The Rapper is another man to spurn the notoriously selective label’s inquiries back in the era of the bidding war. Corroborated by TDE President Terence “Punch” Henderson himself, the Chi-Town native acknowledged that talks were held but the parties never came close to inking a deal:

“They didn’t almost sign me, they wanted to sign me. Don’t say it like that, though. I turned down being signed.”

Kanye West & Birdman

Kanye West arriving at NYFW 2018 - Rob Kim/Getty Images

By way of a conclusion, it seems only fitting to highlight two prospective deals that could’ve altered hip-hop as we know it. Prior to cementing his legacy with his mentor Jay-Z, Kanye West was just an aspiring producer with a wealth of creativity at his disposal. Although he infamously revealed how he played a label “'Jesus Walks' and they still didn’t sign me” on “Last Call,” what’s less publicized is that he very nearly signed to Cash Money. In another excerpt from The College Dropout’s closer, Kanye discusses how one of his artists got signed but bypassed his production company. In an effort to cut his losses, Ye “went down and tracked the beats from him” and took the money. As it turns out, that artist was Mikkey Halsted and he explained to DJ Booth that his deal with Birdman nearly led to Kanye’s “Kanman Productions” getting a place in Cash Money history:

“I said, ‘Kanye, man, they wanna fly me out and I told them they got to fly you out too.’ So Kanye went to New Orleans, brought all of the music from all the artists, and calls me and says, 'Man, they offering me a deal for everybody on Kanman Productions. Everybody. Me, your sister, myself, Go Getters, the whole nine. They just wanna make it like Cash Money Midwest.'" A deal that would’ve prohibited him from dealing with Roc-A-Fella, the concept of Ye becoming an extension of the Williams brothers’ imprint is fascinating from every angle.

Eminem & Fat Joe

Eminem performing at 2005 MTV Movie Awards - Kevin Winter/Getty Images

Last but not least, Terror Squad mastermind Fat Joe may have carved out a lucrative career for himself, Big Pun, Remy Ma and DJ Khaled but he’s spoken candidly about the biggest misstep of his life:

“Man I got so many regrets. The biggest is that Eminem gave me so many demos – six different times he approached me and I didn’t sign him. Shame on me.”

A tale that’s perpetuated throughout the eras, these “what could’ve been” scenarios will always give us a fascinating window into an alternate hip-hop universe and the drastic shifts in the landscape that were one change-of-heart-away from being set in stone.