Freestyling With Eminem, 1999, In The Loder Files

Tales from Detroit, and an off-the-cuff rap with his late friend Proof.

When you've been interviewing people for, oh, a hundred years or so, you build up quite a backlog of banter and chat. A lot of this stuff is inevitably ephemeral — the day will surely never come when anyone cares what Vanilla Ice ever had to say about anything. On the other hand, it is kind of interesting to look back on the vintage natterings of people who are still on the scene and still entertaining us, either with their work or with their dotty behavior.

We've been exhuming a ton of this stuff over the last several months — interviews from the vaults going back not only to the early '90s, but even beyond. Most of these ancient tapes are fun in one way or another; some are scary, which is even more fun. We're going to be posting these old interactions every Tuesday from now on, and if some of what you see seems a little silly at times, well, the past is filled with silly things. Much like the present.

The hurricane of shock and horror that would soon start blowing in from the high seas of political correctness was still a ways off when we went up to Detroit to talk to Eminem in the late winter of 1999. (Check out our full interview from that visit in this '99 feature.) The 26-year-old rap phenom had just released his first major-label album, The Slim Shady LP, and "My Name Is," the cute single and video that started selling it, gave little indication of the man's remarkable artistic range, or of how deeply dark his humor could be. That would all become clear very soon, though.

Em's daughter Hailie was three years old at the time we met. His relationship with her mother, Kim, was ... troubled, let's say. One of the Slim Shady tracks, called " '97 Bonnie & Clyde," depicts him taking Hailie for an ominous late-night drive to the beach. When Hailie asks where her mother is, Em says, "She's takin' a little nap in the trunk." Rarely, if ever, had psychodrama been conveyed with such electrifying directness.

A lot of people have found the unhinged violence in some of Eminem's lyrics totally deplorable — all the more so for being at the same time hilarious. Having grown up in fatherless poverty, the man clearly had some issues to work through, not least with regard to his mother, Debbie Mathers, who was also a target of his embittered acrimony. (Em said Debbie was so unreliable a parent that he had to raise his younger brother, Nate, pretty much on his own.)

That day in Detroit, he took us to one of the houses he'd lived in as a kid, and we sat down on the front steps. Em had passed through a lot of places over the years, and he'd stockpiled a lot of stories, many of which he told us. At the end of the afternoon, his friend Proof showed up. Proof and Eminem had been friends since high school, and Em had been a member of Proof's much-admired rap collective, D12, until he hooked up with Dr. Dre in Los Angeles. Now Eminem was a bigger star than Proof would ever be, but they were still tight. (Em's very big on loyalty: D12 was the first act he signed when he started his own label, Shady Records; and he also found a small part for Proof in his 2002 movie, "8 Mile.")

After we'd finished talking, Em climbed behind the wheel of his van to take off. He lingered a bit to talk to Proof through the window, though, so we asked the two of them if they'd like to freestyle a little for us, like in the old days. Em slipped some beats into the van's sound system, and they got right into it. To me, this is one of the great rap moments — for Eminem's wicked improvisational skill, for the way he and Proof vibe together, for the love they clearly have for what they're doing.

Eminem, of course, went on to worldwide acclaim. Proof recorded a solo album in 2005, and Em took him out on the Anger Management Tour to help promote it. The record didn't do much, though, and the following year, back home in Detroit, Proof was shot dead one night during a bloody fight at a local club out on 8 Mile Road.

Enjoy digging through The Loder Files? You'll find more here, and there's much more to come from the vaults — check back every Tuesday!