Mikey D: The Best Rapper You Never Heard Of

By Akoto Ofori-Atta


Because behind every pop star is an unsung hero who got left behind.

The story of LL Cool J and battle rapper Playboy Mikey D is classic ‘80s street lore: Folks claim LL, the allegedly less talented MC, studied his boy’s trademark technique and absconded with it, making pop history by snatching the career that should have been Mikey’s. The victim, the shafted favorite, then spiraled into a less remarkable life. The superstar, naturally, is mostly to blame.

The real story, though, isn’t so clear-cut. 

Mikey, aka Mike Deering, says that he too was offered a record deal with Def Jam Recordings , which celebrates its 30th anniversary this year. The hazel-eyed MC certainly had what it took: pretty-boy looks, dope rhymes, a devoted following. So why isn’t Mikey’s name next to LL’s in the annals of Def Jam’s rich legacy?

Ask anyone from Queens who came of age in the ‘80s, and they’ll tell you they would have bet that Mikey would be the star.

The two were slated to face off in a high-school rap battle, but backstage they bonded over their similarities.

“LL wasn’t even close,” says Jelani Cobb, director of African-American studies at the University of Connecticut, who went to middle school with LL Cool J. “Mikey was widely thought of as the best in Queens.”

BW with LL Cool J and boombox

LL Cool J and MIkey D shaking hands

Today, Mikey D, a neighborhood celeb/street legend, is living far outside his beloved Queens. Why? He’s a bit mysterious about all that, refusing to disclose where he lives or what he does for a living. But when you pin him down, he’s eager to chat, teeming with encyclopedic knowledge about hip-hop, cheerfully recounting the time he first met LL back in ‘83 — a tale that contradicts the perceived central tension of their friendship/rivalry.

As he tells it, the two were slated to face off in a high-school rap battle, but backstage they bonded over their similarities.

“We just bugged out at how much we sounded alike,” says Mikey D, now 46. “So instead of battling, we just rocked together.”

At the time, LL, whose real name was James Todd Smith, was going by the moniker “J Ski.” Mikey D gave LL — which stands for “ladies love” — his stage name, which the Grammy-winning rapper has acknowledged . It’s a bit of history that Mikey shrugs off.

“I don’t like to toot my own horn,” he says.

That’s curious, coming from a dexterous battle rapper whose entire reputation was built on claiming to be the best while destroying those who tried to claim the same. Count pioneering rapper Melle Mel among Mikey D’s victims.

In 1984, flush with success, Mikey D invited LL to join a group called Sensational 5, and that’s where their respective paths to pop acclaim and pop obscurity diverged.

I just wanted the respect of my hood. LL wanted more. 

As LL was preparing for superstardom — Cobb recalls an assured but unknown 16-year-old LL distributing autographs to classmates — Mikey D was embarking on a 27-year battle with alcohol. He says that when Def Jam came calling, he turned them down. He was convinced they only wanted him to keep him away from the competition. (Def Jam did not respond to interview requests.)

“I just wanted the respect of my hood,” Mikey said. “LL wanted more. When he would spend his last dime trying to get to a meeting, I would spend my last dime on a 40-ounce and then I’d try to hustle a ride to the meeting.”

But don’t get it twisted. There really was a feud, one that would cast LL as the biter who stole a hood legend’s style, one where the faint line between plagiarism and influence becomes blurry. On LL’s 1987 hit “I’m Bad,” he rapped, “Forget Oreos/eat Cool J cookies.” This was, to most folks in Queens, including Mikey D, a not-so-subtle theft of Mikey’s classic battle rap line, “I am imperial/Pro material/Kids all over eat Mikey D cereal.” (LL Cool J did not respond to interview requests.)

The two would spend the next 20-something years in beef. Mikey D went on to join rap group Main Source in 1991 , and Madonna later sampled their song “What You Need” for her 1994 hit “Human Nature.” For a while, Mikey stopped recording, disheartened by the gangsta turn rap had taken. Meanwhile, LL, well, became LL. They’d sometimes cross paths over the years, occasionally exchanging “fuck you’s” when they did. But in a recent song , Mikey D admits he was full of unjustified rage.

It took sobriety for him to reach out to LL and apologize, and they’ve since made up, says Mikey D, now 18 months clean. Today, Mikey D is recording mixtapes again, performing and enjoying the trappings of esoteric fame: an unexpected career resurrection thanks to some hipster fans in Russia, Germany, London and Italy.

So yes, LL got the record deal. But Mikey D says he still has the thing he always wanted: respect as one of the best battle rappers ever to come out of Queens — and, he says, he’s still collecting royalty checks from that unintended collaboration with Madonna.

A victim? Not so much.