It’s easy to forget a time when Eminem’s choice collaborators were rooted in hip-hop. From RBX and Sticky Fingaz on “Remember Me,” to Xzibit on “Don’t Approach Me” and “Say My Name,” to Redman on “Off The Wall.” The list goes on. While glimmers of the past occasionally shine through (think “Chloraseptic Remix”), Em has seemingly embraced the pop-ballad, aligning himself with singers like Pink, Skylar Grey, and Beyonce. The creative choices on Revival were maligned by long-time fans, leaving many pondering the catalyst of this new direction.

It’s strange to reflect on a time when 50 Cent used to be a fixture on Eminem’s albums. Since his early millennium signing to Shady Records, Fifty has appeared on Encore, the 8 Mile Soundtrack, The Re-Up, and Relapse. Conversely, Em appeared on Get Rich Or Die Tryin’, The Massacre, Curtis, and Before I Self Destruct. Sadly, Relapse single“Crack A Bottle” signified the end of an era, pouring proverbial liquor to the curb in memory of the once mighty kindred spirits.

For the most part Eminem and 50 Cent come from disparate schools. Their respective discographies share little in common, save for involvement from Dr. Dre, and their approach to lyricism and flow seem cut from different cloths altogether. Consider Em’s other wingman Royce Da 5’9”, who has clearly drawn influence from some of Eminem’s chief inspirations; Redman and Masta Ace come to mind. When Royce and Em collaborate, they sound like two sides of the same coin - Bad and Evil.

50 hails from a different school altogether. The product of Southside Jamaica Queens, 50 Cent quickly became a dominant force on the mixtape circuit. More aligned with the rugged poetry of Raekwon than the dexterous bars of Pharoahe Monch, Fif slung music like a true hustler, peddling mixtapes with a generosity Em fans have never known. And while their roots are no doubt different, one uniting factor does stand out. Neither rapper has any qualms about making enemies.

50 Cent’s “How To Rob” seemed to target the entire game, drawing animosity from Jay-Z, Ghostface, Big Pun, and more. That isn’t even counting some of his more recent feuds including notorious tilts with Rick Ross and Jadakiss. Eminem’s own shit-list has led to some legendary exchanges, going through prominent feuds with Benzino and Ja Rule; Em was even about to go at Suge Knight until Dr. Dre urged him not to.

The only person to have amassed more beef than Eminem might be 50 himself. Yet for better or worse, the pair never failed to move as a unit, inheriting one another’s beefs without hesitation. The loyalty they had for one another made for one of hip-hop’s most unlikely and fruitful partnerships. In fact, loyalty and violence were two of the dominant themes behind many Eminem and 50 Cent collaborations.

Consider one of their more underrated ones, The Massacre’s “I’m Supposed To Die Tonight.” While Em doesn’t actually have a verse, he steps into the producer’s chair with capable hands; his menacing instrumental is a character in itself, a dark lullaby over which 50 can freely embody hip-hop’s Grim Reaper. Another prominent Massacre cut is “Gatman & Robbin,” which finds Em and 50 tauntingly flaunting their status as hip-hop’s dynamic duo. Despite the cartoonish motif, the main thematic crux of is undying loyalty. The pair seems to embolden one another. “You touch Shady I’ll leave you dearly departed,” raps 50, a line later mirrored by Em. 

It goes without saying that “Patiently Waiting” is their magnum opus. Once again, Em laces 50 Cent with another ominous instrumental, pioneering a sound that came to define the bulk of their early work. G-Unit’s “My Buddy” found Eminem occupying a similar musical headspace, laying down a haunting choral arrangement, transforming a traditional gun track into of something from a nightmare. 8 Mile’s “Love Me” follows the same trend, with Eminem once again laying down some minor key, eerie string arrangements; 50 was in fine form here, taking shots at Lil Kim, D’Angelo, and Lauryn Hill in a ruthless parting shot.

In 2004, Eminem’s Encore seemed revealed a slight musical shift. “Never Enough” found both rappers trading verses over an energetic beat from Dr. Dre, trading in somber reflection for hyperactive braggadocio. “Spend Some Time” is also a marked departure for them, although 50 retains some of his no-fucks-given demeanor.  "You have very nice lips,” he raps. “With my imagination, I could see her suckin' my dick.”

Despite the deviation, Em and 50’s aforementioned work on The Massacre seemed to find the duo once again embracing their base nature. “Jimmy Crack Corn” felt like a more playful successor to “Patiently Waiting,” with both rappers coming through with flows simultaneously lazy-yet-hard. Before I Self Destruct cut “Psycho” may very well have been a Relapse 2 leftover (a personal theory), with Eminem’s foray into horrorcore territory and dexterous flow rubbing off on Fif.  As for “Peep Show” and “My Life,”well...some things are better left unsaid.

It has currently been years since 50 Cent and Eminem collaborated. The game’s landscape has altered dramatically, as has Em’s music. The same may very well be said about 50, but his output has slowed dramatically. That’s not to say the respect is gone; Em’s recent ode to 50’s “Places To Go” verse was a respectful and endearing homage. Yet the fact that their last released collaboration with the Adam-Levine assisted “My Life” makes for a bit of a tragic ending, to quote Em’s latest album.

It’s hard to tell what a 50 Cent and Eminem collaboration might sound like today. For one, Em has largely abandoned his desire to produce his own beats. With that, much of his dark-carnival aesthetic has fallen to the wayside, replaced by a newer, pop friendly entity. It wouldn’t be surprising to see the pair unite for a last hurrah, but the idea of them revisiting their iconic sound is unlikely to say the least.

It may be uncouth to beg an artist to revert to their older work, but the idea of Eminem and 50 Cent reuniting for an Alex Da Kid or Rick Rubin produced radio single is a bittersweet one. Yet the recent “Chloraseptic Remix” was seen by many as a step in the right direction. There was something undeniably refreshing about seeing Eminem once again trading bars with rappers. Plus, 50 Cent does have an album on the way. Maybe there’s still time. Ideally, they can hit up Scott Storch to procure this banger or die tryin’; with a sound evocative of Em’s vintage aesthetic, it seems like the perfect opportunity to end their storied legacy on a high note.

For now, relive some of their greatest hits with our playlist below.

Eminem & 50 Cent: The Hits