A stand-up comedian does ten to fifteen minutes of material regularly. When she's headlining a show, she may do up to an hour. No matter how much she needs new material, she's entertaining a new audience every show, so her material is mostly repeats.
Not so the DJ. He's on live radio four to six hours for five days a week and his audience is fairly loyal. With humor, a DJ changes from a voice-over announcer to a personality. The memorable DJs of the past ten years (like Larry Lujack, Howard Stern, Charlie Tuna, Don Imus, and Gary Owens) all made their reputation through the humor they presented, not the records they played. No one needs a more constant supply of fresh humor material.
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When you think of freelancing, what is the first thing that comes to your mind? You probably think of a writer, novelist or journalist right off hand. That is primarily because for centuries, the only real job you could have as a freelancer had to do with your mastery of the written word.