I remember reading a book about Abbott and Costello and one of them fell behind on their taxes and the rates at their income were so high that they could never catch up.
The IRS just took their property.
Happened frequently
That was probably due to a manager who was inept or stealing from him. That happened to Errol Flynn, he thought he was set for life and had entrusted his money to his manager. The guy died and all of sudden Flynn is about broke, the guy spent all of Flynn’s money on high living and a private plane.
Flynn had a hard time ever paying the IRS off. That happens frequently to entertainment and sports figures. They always trust the wrong person.
Also to shield income in that era a lot of people, like business people, and entertainment people, had personal corporations formed, their money was paid into that, then they took what money they needed to live on and paid a lower tax rate.