You guys are thinking of the guys who didn't "fall off".
Biz Markie has been DJing since the beginning, he gets thousands a gig and has at least 2 a week. Lives in a mansion.
Cappadonna however didn't drive a cab. He did something they call "gypsy cabbing" where you drive your own car around NY asking people if they need rides. You usually pick up criminals and take them to do dirt. He has somewhere around 6 kids, rap money ain't that big. At their prime less famous Wu Members were making about $50,000 a year each. That was 3-5 years max. Even RZA aknoweges that Cappa only accumulated about $200,000 for his efforts.
In a few years, Chingy will have a story he's over $600,000 in debt to his label.
Amil works at K-Mart in Kansas City. She still has a fly car tho.
But you have to understand, she never had her own album, just feature money. Tours put some cash in her pocket, but she was with the Roc, so she was flashy. Jay takes care of people around him, but once your out his circle, you're on your own. She made $80,000 max her whole career. I'm sure she got gear and jewelry from just hanging around Jay.
Ma$e ran off to become a Pastor and broke his contract with Puff for 5 albums. Puff, being Ma$e's friend felt Ma$e should be allowed to quit rap to persue spirituality, so he released Ma$e from contract(losing Puff millions)with a clause that before Ma$e could return to music freely he was obligated to finish his 5 album deal. He returned with "Welcome Back"(album 3 of 5), missed shows, did lackluster chart numbers, then wanted to jump ship to G-Unit and go back to being "Murder Ma$e(cursing, talking about killing, basically grimier than Bad Boy Ma$e). Puff felt disrespected and now won't release Ma$e and will take a huge percentage of any profits Ma$e ever makes off music.
Most past rappers end up living a regular life working warehouse jobs where they're not publicly seen, or living with family and other artists managing off meager(I'm talking $50-300/month)royalties. Alot end up selling drugs, on drugs in crackhouses, go back to the streets if that's where they were before. Start pimping groupies, or get a rich groupie and mooch off of her.
I see this sh*t everyday, I stopped naming names on this site, I'm cutting off my own foot by doing so. But if you watch an episode of rap city from the late 90s about 90% of the people on that show are doing one of the things I said. Some people who just had a big hit a year ago are doing stuff on the list I said.
Rap does not make you rich. As Black Folk we always talk bigger than what we do. Don't majority of Black folk in the military drive cars and rock Jewelry they can't afford? Don't drug dealers buy extravagant things, but dodge child support, get locked up have no money for bail? What makes you think rappers live life different?
When the ride ends, it ends. I've had to play a multiplatinum artist's way in the club after he hitched a ride with me because his "momz be naggin him to get a job", so he wanted to go holla at sum biches. Once he got in the club "oh sh*t, it's MC git busy!!!" V.I.P. treatment, free drinks, got to meet a dude from trillville, hung out with Darius McCrae(Eddie Winslow on that show with Urkle)and Xzibit, smoked a few blunts with some model chicks in the parking lot. He went in the cut somewhere, got groped up real quick by one of the model chicks(she was bad too!), then we hopped in the car and I took him home...to his mama.
I don't make this sh*t up, wish I could say I did.