Larry Jackson’s rise was fast-tracked by a pair of industry titans: Clive Davis at RCA and J Records and Jimmy Iovine at Interscope. The latter relationship put him in the middle of the action when Iovine and Dr. Dre founded Beats, which morphed into Apple Music in 2015.

Thereafter, Jackson has been behind virtually every collaborative co-sign to the service—a list that includes Drake, The Weeknd, Taylor Swift, Frank Ocean, Ye and Nicki Minaj. Now, following his September 2022 exit from Apple Music, where he served as global creative director, Jackson is the subject of intense industry speculation as he plots his next move.

In this excerpt from his interview for Rainmakers, Jackson recalls his years working with the two legendary label heads.

Clive is tough, demanding and expects a lot. I imagine you went immediately into the ringer.
First day on the job was September 11, 2000. I was in a bungalow at the Beverly Hills Hotel, the full speaker setup. That was my introduction to the nine-hour producer/songwriter meeting, a nonstop parade of music at blaring volumes. Every producer wanted to come and play music for Clive, learn from Clive. It was Clive, Keith and me that first day. Then back to New York and working out of the Waldorf Astoria, which was equally special. I was at the label for 10 amazing years; I started in September of 2000 and got fired in October of 2010.

What was some of the music you worked on?
Chronologically, Luther was the first thing I did, then O-Town. We worked on Santana, then [RCA Music Group SVP A&R/ Marketing] James Diener brought in Gavin DeGraw. But what really gave me confidence was when we signed Tyrese—on my 21st birthday at Clive’s home in Pound Ridge. I’d done a label deal with The Underdogs [Harvey Mason Jr. and Damon Thomas] a year prior, and they delivered Tyrese’s “How You Gonna Act Like That.”

Clive would call me between 11pm and midnight Monday through Thursday and ask about BDS or what I thought about a strategy for Maroon 5 or what I thought about this Pop Idol thing Simon Fuller came in with. And then, when we got Arista after L.A. [Reid] left for Def Jam, he gave me this huge binder of the 70 artists on Arista and said, “You’ve got to listen to all this; what are the hits?” It was a massive education.

You were understandably shook when you were suddenly shown the door, but that was the start of the Jimmy Iovine era for you.
The exit from Sony was unexpectedly the gift of all gifts. I found that you don’t need that many people on your side, just the right person—the right sponsor, the right believer. And that was Jimmy. But our relationship was already strong. We’d discussed the possibility of my coming to Interscope two or so years earlier. At the time, Clive and I were producing Whitney Houston’s last studio album, I Look to You, and she and I were enormously close. I wanted to complete what we’d started, so I stayed largely because of Whitney but also for Jennifer [Hudson], whose debut album I was finishing.

The evening of the day I was unjustly fired for cause, Jimmy reached out, saying, “Can you come to work on Monday?” I said, “Dude, I just got sucker-punched. But I deeply appreciate and am flattered by the offer and your continued interest. Let me process what just happened; I’ll get back to you at the top of the week.”

About a year before I was fired, I’d signed a new four-year deal with Sony to become president of Arista. But, in retrospect, it wasn’t for the right reasons; in that moment, I wasn’t as adventurous or as fearless as I should have been. My creative thirst wasn’t being quenched, and the experience had become something of a hamster wheel. After a while, I wondered, what am I trying to prove? The world is as big as you make it, and there’s nobody who gets that like Jimmy—nobody. And I’m so glad to have had this left-brain/right-brain education from Clive and Jimmy.

There are certainly some fundamental differences between them.
The first week I was at Interscope, I was sitting in a meeting with Jimmy. Lady Gaga’s debut album, Fame Monster, was at a gazillion records sold that week, and I asked Jimmy, “Do you know how much it sold this week?” He gives me a look and snaps, “I haven’t read SoundScan in five years—I don’t fucking know what it sold. Go ask Clive that question.” That’s when I realized I wasn’t in Kansas anymore. I was now working with someone coming from a different side of the brain with a different intent relative to where he saw the business going. It didn’t have anything to do with even monolithic metrics but everything to do with new technologies, new distribution channels, consumer products like Beats by Dre headphones… It was an amazing rewiring of my brain, accessing something I hadn’t had a chance to tap into before Jimmy.

Read the complete interview here.