8. Outsidaz, “Rush Ya Clique”
In the late ’90s, before Em’s debut album hit, he’d already linked with some of underground hip-hop’s best artists — like this East Orange, New Jersey group that spawned Rah Digga. It’s Shady at his most exuberant, still polishing the persona that would endear him “to the weird kids with piercings in more than one ear.”
7. Shabaam Sahdeeq, “5 Star Generals”
Another late-’90s joint — this one the B-side of Sahdeeq’s 1998 single “Sound Clash.” Em popped up on a number of Rawkus Records projects around the same time, like a solo track on the Soundbombing II compilation, but this posse cut stands out for also featuring the underappreciated Kwest tha Madd Ladd.
6. Madd Rapper, “Stir Crazy”
The original hip-hop troll (in his day job, Deric “D.Dot” Angelettie was a Bad Boy producer) had already put together 50’s breakout street single “How To Rob,” but grabbed Em for this track off Tell Em Why U Mad. “Shady said it, Shady meant it, I stay demented/I’ll throw a stroller at you, with a baby in it!”
5. Drake, Kanye West, Lil Wayne, and Eminem, “Forever”
This one’s not so much a guest verse as a clash of titans from a LeBron James documentary soundtrack. But the 2009 song, which marked Drake’s confident entry into rap’s upper echelon, reminded people that even while on hiatus, Em could always come back and fuck the game up. (It also foresaw his slide into increasingly laborious technical flows and dad jokes, which is why it’s back here at #5.)
4. Notorious B.I.G., “Dead Wrong”
Biggie never released the original, so when it came time to put together the posthumous Born Again, there was only one logical choice as to who could come anywhere close to the Teflon Don’s horrorcore-adjacent lyrics. And Em doesn’t disappoint, ditching the Slim Shady whine in order to ride a neck-snapper of a Hitmen beat.
3. Xzibit, “Don’t Approach Me”
Em and X to the Z got tight touring in 2000, and that friendship led to a slew of bangers — including this one, where they ditch the posturing and engage with the frustration that comes with stardom. An early look at Em grappling with the fallout of his sudden fame.
2. Dr. Dre, “Forgot About Dre”
The 2001 track is one of the Doctor’s best lyrical showings ever. Thankfully, his ghostwriter stuck around to perform his own verse as well. A hilarious mix of storytelling and Slim Shady nihilism, it remains undeniable… as long as you can ignore the White people butchering it in karaoke bars.
1. Jay-Z, “Renegade”
No real mystery here. By the time The Blueprint came out, most of Em’s output had been psychopathic smartassery. But this, the only feature on Hov’s whole album, complemented Jigga perfectly, making for a self-aware critique that articulated hip-hop’s discomfort with mainstream relevance and dismantled pearl-clutchers’ hypocrisy like no other artists could have.
Read more: The 7 Least Embarrassing Interracial Rap Duos, Ranked