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I don't think he's concerned about losing money specifically - but I think he is concerned about his overall consistency. When you look at Jay's career the main thing that gives him his status is is overall consistency. He's never "fallen off"...his albums always consistently go platinum and debut at #1 on the charts. He's also very consistent in terms of quality - his "bad" albums are way better than most rappers that have "bad" albums. BP2 and Kingdom Come are probably his worst albums in terms of reviews and they both are still solid albums in a career discography. Noone in rap has done what he's done for anywhere near as long as Jay has, and it's somewhat like an undefeated streak, like Floyd Mayweather or some other athlete.
I think that this streak puts a TON of pressure on him, and you can see it at different points of his career. It's almost like he has two sides of his brain always fighting with each other. Before an album comes out he's always talking about how it's gonna be different and "this one isn't gonna sell" like he wants to have a disclaimer in place because he's self-conscious about it. He takes a risk by dropping a double album in BP2. While recording that album he records some of his best work in Hovi Baby, Meet the Parents, Excuse Me Miss, etc. But he decides to make it a double album, probably thinking of his legacy in terms of a Life After Death or an All Eyes on Me, and in doing that the album ends up a bloated with a ton of guest features, filler songs, "the gift and the curse" concept which didn't make sense, a Tupac cover as a single, etc.
So then comes the Black Album...up to that point he was dropping number 1 albums every year which was and still is unheard of. "Retiring" took some of that pressure off in that now he isn't expected to drop every year. I think his intention was to not have the pressure to still sell as much with each album but it's like the other side of his brain wins out and he caves. The Black Album was supposed to be his record that didn't care about sales - no promotion, no radio friendly singles, minimal guest spots, etc, the legendary producers on every track concept, etc. But he ends up caving and does a Change Clothes, does promotion, etc. Still a great album, but not true to the original concept, probably because he was concerned with it doing numbers and keeping his streak alive.
Then he retires and comes back with Kingdom Come. It's already been mentioned that he was originally going to release it under Shawn Cater and not the Jay-Z name. He didn't do that, and it was definitely promoted heavily. He did use different topics on this album than he had in the past, but got criticized for doing that. The album did big numbers as always though, and his streak was still alive. Then he drops American Gangster (which is a classic in my opinion) but it's like he's so self conscious about what people think about him he does this concept album tied in to the movie just as an excuse give the critics what they want after KC - him rapping about selling drugs. He still tries to put disclaimers out there on sales - it being a concept album and them him pulling it from iTunes because he didn't want individual singles sold. It's like he's really TRYING to run away from the streak at this point. But it STILL did numbers, and was well reviewed by critics.
So he comes back with BP3. Drops D.O.A., talks again about not caring about sales. But he ends of doing singles with Rihanna and Alicia Keys, the album does huge numbers, and he gets his first number one single (which is still crazy to me).
In some ways I think the best thing that could happen for Jay as an artist would be to release a REAL dud that doesn't sell at all, freeing him from his streak, and allowing him to let the other side of his brain win and make some music without worrying about falling off. But on the other hand releasing a dud would probably do the opposite and encourage him to prove everyone wrong and do another "big sales" album.
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