entertainers are not paid like the average 9-5 joe because most are considered self employed. the taxes aren't always automatically deducted.
redd foxx had the option to be paid in checks or cash and opted for cash after being cheated/shorted by promoters. even if he'd accepted checks, he was still responsible for reporting the earnings and paying the taxes accordingly. clearly, he didn't do this.
if you're smart, you work with a reputable accountant/financial advisor to ensure your taxes are paid quarterly. if not, well... you've heard the tragic stories. it doesn't have to be this way, but poor management/planning can get the best of anyone.
redd further compounded his issues by thinking he could get away with not reporting some earnings (as well as failure to pay), but didn't realize the same companies/people that paid him were obligated to report his earnings as well. failure to pay his own property taxes was the nail in the coffin.