>No way he's made or been on atleast 20 songs that have made the top 100 charts

You're over-estimating how much recording artists get paid.

I saw a story of Lisa Lopes talking about how, at the peak of TLC's popularity, they were taking home ~$50k/year each. That was despite having just released one of the best-selling albums ever at the time, CrazySexyCool, which went 12x platinum. It later came out the group only got 56¢ per album sold - at a time when CDs cost $18 each.

"Industry rule number 4080: record company people are shady." -A Tribe Called Quest