Historically, Lisp has been good at letting hackers have their way. The political correctness of Common Lisp is an aberration. Early Lisps let you get your hands on everything. A good deal of that spirit is, fortunately, preserved in macros. What a wonderful thing, to be able to make arbitrary transformations on the source code.
Classic macros are a real hacker's tool-- simple, powerful, and dangerous. It's so easy to understand what they do: you call a function on the macro's arguments, and whatever it returns gets inserted in place of the macro call. Hygienic macros embody the opposite principle. They try to protect you from understanding what they're doing. I have never heard hygienic macros explained in one sentence. And they are a classic example of the dangers of deciding what programmers are allowed to want. Hygienic macros are intended to protect me from variable capture, among other things, but variable capture is exactly what I want in some macros.
A really good language should be both clean and dirty: cleanly designed, with a small core of well understood and highly orthogonal operators, but dirty in the sense that it lets hackers have their way with it. C is like this. So were the early Lisps. A real hacker's language will always have a slightly raffish character.
A good programming language should have features that make the kind of people who use the phrase "software engineering" shake their heads disapprovingly. At the other end of the continuum are languages like Ada and Pascal, models of propriety that are good for teaching and not much else.
To be attractive to hackers, a language must be good for writing the kinds of programs they want to write. And that means, perhaps surprisingly, that it has to be good for writing throwaway programs.
A throwaway program is a program you write quickly for some limited task: a program to automate some system administration task, or generate test data for a simulation, or convert data from one format to another. The surprising thing about throwaway programs is that, like the "temporary" buildings built at so many American universities during World War II, they often don't get thrown away. Many evolve into real programs, with real features and real users.
I have a hunch that the best big programs begin life this way, rather than being designed big from the start, like the Hoover Dam. It's terrifying to build something big from scratch. When people take on a project that's too big, they become overwhelmed. The project either gets bogged down, or the result is sterile and wooden: a shopping mall rather than a real downtown, Brasilia rather than Rome, Ada rather than C.
Another way to get a big program is to start with a throwaway program and keep improving it. This approach is less daunting, and the design of the program benefits from evolution. I think, if one looked, that this would turn out to be the way most big programs were developed. And those that did evolve this way are probably still written in whatever language they were first written in, because it's rare for a program to be ported, except for political reasons. And so, paradoxically, if you want to make a language that is used for big systems, you have to make it good for writing throwaway programs, because that's where big systems come from.
Perl is a striking example of this idea. It was not only designed for writing throwaway programs, but was pretty much a throwaway program itself. Perl began life as a collection of utilities for generating reports, and only evolved into a programming language as the throwaway programs people wrote in it grew larger. It was not until Perl 5 (if then) that the language was suitable for writing serious programs, and yet it was already massively popular.
What makes a language good for throwaway programs? To start with, it must be readily available. A throwaway program is something that you expect to write in an hour. So the language probably must already be installed on the computer you're using. It can't be something you have to install before you use it. It has to be there. C was there because it came with the operating system. Perl was there because it was originally a tool for system administrators, and yours had already installed it.
Being available means more than being installed, though. An interactive language, with a command-line interface, is more available than one that you have to compile and run separately. A popular programming language should be interactive, and start up fast.
Another thing you want in a throwaway program is brevity. Brevity is always attractive to hackers, and never more so than in a program they expect to turn out in an hour.
Of course the ultimate in brevity is to have the program already written for you, and merely to call it. And this brings us to what I think will be an increasingly important feature of programming languages: library functions. Perl wins because it has large libraries for manipulating strings. This class of library functions are especially important for throwaway programs, which are often originally written for converting or extracting data. Many Perl programs probably begin as just a couple library calls stuck together.
I think a lot of the advances that happen in programming languages in the next fifty years will have to do with library functions. I think future programming languages will have libraries that are as carefully designed as the core language. Programming language design will not be about whether to make your language strongly or weakly typed, or object oriented, or functional, or whatever, but about how to design great libraries. The kind of language designers who like to think about how to design type systems may shudder at this. It's almost like writing applications! Too bad. Languages are for programmers, and libraries are what programmers need.
It's hard to design good libraries. It's not simply a matter of writing a lot of code. Once the libraries get too big, it can sometimes take longer to find the function you need than to write the code yourself. Libraries need to be designed using a small set of orthogonal operators, just like the core language. It ought to be possible for the programmer to guess what library call will do what he needs.
Libraries are one place Common Lisp falls short. There are only rudimentary libraries for manipulating strings, and almost none for talking to the operating system. For historical reasons, Common Lisp tries to pretend that the OS doesn't exist. And because you can't talk to the OS, you're unlikely to be able to write a serious program using only the built-in operators in Common Lisp. You have to use some implementation-specific hacks as well, and in practice these tend not to give you everything you want. Hackers would think a lot more highly of Lisp if Common Lisp had powerful string libraries and good OS support.
Could a language with Lisp's syntax, or more precisely, lack of syntax, ever become popular? I don't know the answer to this question. I do think that syntax is not the main reason Lisp isn't currently popular. Common Lisp has worse problems than unfamiliar syntax. I know several programmers who are comfortable with prefix syntax and yet use Perl by default, because it has powerful string libraries and can talk to the os.
There are two possible problems with prefix notation: that it is unfamiliar to programmers, and that it is not dense enough. The conventional wisdom in the Lisp world is that the first problem is the real one. I'm not so sure. Yes, prefix notation makes ordinary programmers panic. But I don't think ordinary programmers' opinions matter. Languages become popular or unpopular based on what expert hackers think of them, and I think expert hackers might be able to deal with prefix notation. Perl syntax can be pretty incomprehensible, but that has not stood in the way of Perl's popularity. If anything it may have helped foster a Perl cult.