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Comedian Lewis Black is 65, but his audience skews much younger. This creates some unusual challenges for the Daily Show commentator—like finding a way to do a live comedy special without isolating fans closer to his own age. "I can’t put it on Yahoo, because 40 percent of my audience isn’t going to watch it on their computer. And HBO, those fucks, wouldn’t do it," he tells us. Fortunately, Black reached a solution; his stand-up special, _Old Yeller, _will air August 24 on Pay Per View and Video on Demand, "so at least, they have all the options." Given his cross-generational appeal, we asked the irascible comic to offer some advice to young people. He agreed, though it wasn’t his subject of choice. "I thought GQ was going to call me up and ask me about my wardrobe, because it’s getting better every day," Black chuckled. "But they don’t pay attention to my clothes, those fuckers."

"One of the most important things, especially when you’re leaving school, is to realize you’re going to be dealing with a lot of idiots. And a lot of those idiots are in charge of things, so if you’re in an interview and you really want to tell the person off, don’t do it. When people ask me, ‘Gee, why did it take you so long to have a career?’ it’s because I really thought that my criticism mattered to these people. It never crossed my mind that these people maintain their jobs. You’re going to see them again. And not only are you going to see them again, but the next time, they’re going to be in an even higher position they don’t deserve."

"Remember: you’re living through a major shift. We’ve gone from whatever we were as a society, to whatever the fuck words they’re using to describe it: a digital society. We’re in the middle of that. In the future, a lot of this stuff will be integrated. Which it’s not right now, because this is chaos."

"It’s a big thing now: A lot of people want to be assistants to celebrities. **If you’re pursuing that, you’re an idiot. **You’re a moron. The shortest distance between two points is not a celebrity, or being next to a celebrity. You want to do what it is that YOU want to do."

"The one thing that I know is key to living a somewhat satisfactory life: you really have to pursue what it is that you want to do. Whatever it is. And realize that, chances are, if you do what you want to do, there is hardly any income. In most instances, initially, there’s not. You have to deal with that. And what you’re going to find is, if you’re actually doing what it is you want to do, income really isn’t as important as people say it is. I was broke for a long, long time, and the only thing that bothered me about being broke was that I occasionally had to borrow money. The rest of the time, I was very happy doing what I was doing.