Jimmy Jam & Terry Lewis Michael Jackson HIStory Bonus Segment + Twin Cities Mailbag Questions
The Questlove Show
iHeartPodcasts
4.6 • 2K Ratings
🗓️ 12 May 2026
⏱️ 23 minutes
🧾️ Download transcript
Summary
In this Questlove Show mini-episode, Questlove revisits the making of Michael Jackson's HIStory with a previously unreleased encore segment from the Jimmy Jam & Terry Lewis interview. Ahmir unpacks the track’s orchestral scale, Boyz II Men vocals, and marathon mix sessions with fellow producers, breaking down why “HIStory” feels like MJ’s “Night of the Living Baseheads” moment.
From there, the conversation pivots to mailbag questions from podcast supporters about Jam & Lewis’ creative synergy, Prince deep cuts, and Questlove’s new Rolling Stone feature ranking 100 essential Prince songs.
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Transcript
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| 0:00.0 | This is an I-Heart podcast. |
| 0:03.1 | Guaranteed Human. |
| 0:05.2 | The Questlove show is a production of I-Heart Radio. |
| 0:17.6 | Slight encore, because I will regret this, and I know you want to go home. |
| 0:22.2 | No, we're good. |
| 0:22.9 | Just answer one question from me. |
| 0:24.7 | Okay. |
| 0:25.8 | I think of your entire discography, your most ambitious song and production ever was the title track to Michael Jackson's history album. |
| 0:38.3 | Just based on all the chaos and all those things happening. |
| 0:42.5 | I think I texted you about it. |
| 0:44.2 | I don't think I asked you about it on the show. |
| 0:46.3 | Okay. |
| 0:47.3 | No, we didn't get that far on the show. |
| 0:49.1 | But the thing is, is that it's so ambitious that it's not a single. |
| 0:57.6 | Right. |
| 0:58.6 | When you're working on filler, and here's the thing, I believe the sign of a true artist is based on the filler. |
| 1:05.6 | If you're talking to Stevie's catalog, I'm not talking about the singles chosen. |
| 1:08.9 | It's our prints, I'm not talking about the singles chosen. I like the filler. Yes. I agree. And I know it's Michael and I know you're able to |
| 1:18.4 | be blinded by the Michaelness of it all. But I mean, why did you guys work so hard on such an |
| 1:26.3 | ambitious sounding song, especially in 95 when I know this wasn't invented yet? |
| 1:32.3 | Right. |
| 1:33.3 | Now with this and everything that's, you know, and I know he's always pushed to the limit, let's go further. |
... |
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