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Both Stern and Freed were famous for "controversial" material. Stern claimed he wanted on his tombstone the words he introduced to radio, "penis and vagina." Freed popularized the phrase "rock and roll" (which suggested sex) and played black musicians on the air that weren't humble, Nat King Cole types.
Both were thrown off the air for scandals in conservative Republican times, after Congressional hearings. Stern's boss, Mel Karmazan (spelling?) testified before Congress about "obscenity" in radio. Freed testified in "payola" hearings, and stuffed the gallery of Congress with his teenage fans.
But it goes beyond these political things, too. Both men were immensely popular, and had huge egos. Both tried to get away with all kinds of things. Freed was stupid with money and got into tax trouble, assuming that he'd always make enough money to catch up. The immense audiences he drew to his Paramount live shows made him believe he was invincible. Stern believed that, because he had conservatives on his show and always mocked Clinton and the Democrats, that he'd be insulated from censorship, and that his immense listenership would loudly protest if he were thrown off the air.
Neither Stern nor Freed were particularly generous people, neither one contributing much to charities or selfless causes (which is pretty standard among all celebrities). Neither one took politics seriously, Stern publicly being silly.
When no radio station would hire Freed, he bounced around from small station to smaller station, dying impoverished and sick with cancer while still trying to get a DJ job somewhere. The IRS hounded him to the end of his life about unpaid taxes. While Stern hasn't sunk that low - yet - it wouldn't be surprising if history repeated itself.
If there is a lesson in this, for future air personalities, it might be that you should always be humble, always have a backup career, and have some solid beliefs - better to go down for a principle than for convenience.
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