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I would suppose that most comedians write, or at least assemble their material at the beginning of their careers. One reason is that when they’re first starting, they can’t afford writers. Bob Hope and Phyllis Diller became so successful that they could then afford to pay for material. Also, once a comic becomes successful and gets more and more bookings, they get too busy to write material. They almost have to depend on writers. Another point is that even if comics can write their own material, they still like to have input from writers because it may be funnier than the material the comic writes for him or herself.
As to comics developing their character, that almost happens automatically. As comedians perform they begin establishing that character, they gradually find their voice and their stage persona is created. Writers can then take advantage of that character and use it to build the jokes. It’s much easier to write for a comic with a strong, established stage presence and character than it is to write for a raw beginner. With the beginner, there is no character to lean on.
Both Bob Hope and Phyllis Diller were funny people on and offstage. Some of the gags they did were the result of adlibs they tossed out during a performance. If they worked well, they included them in the act. Even though both of them could create funny material, they also liked to have input from their writers as I mentioned above. Comedians depend on material so they can never have too much of it.
As a writer, it’s important to know your comic. What material they prefer, which material they won’t us, which type of material works best for them, and so on. If the comic has a strong stage presence, it’s easier for the writers to utilize it in writing the gags. I don’t know if we knew it better than the comic, but we had to know it pretty well.
Two-person comedy is interesting. With the distinct personalities, you can vary the delivery somewhat. The setups have a different cadence and speech pattern than the punch lines. Dean Martin could deliver a straight line in a much different way than Jerry Lewis would present the punch. It’s a good form. I’m not sure it’s better than individual comics. I’m not sure individual comics are better than team comedy. They’re just different.
I’m not exactly sure how George Carlin or Steve Allen came up with their routines. I’m sure they worked hard on them.
Is it easier for a writer to become a comedian or a comedian to become a writer. My advice has always been to decide what you want to become – a writer or a comic. Once you decide, then devote your efforts to that goal. Show business has a way of pigeon-holing people. If you’re a writer, you should only be a writer. If you’re a comic, you should only be a comic. It’s difficult for a writer to become a comedian or a comedian to become a writer. That’s just the way it usually works. Some have made the transition, but it’s not a common one. Go for whichever goal you prefer.