I missed all the fun, all the good C++ answers have already been posted !

This is the weirdest thing I could come up with, I wouldn’t bet it’s legal C99 though :p

#include <stdio.h>

int i = 1;
int main(int argc, char *argv[printf("%d\n", i++)])
{
  return (i <= 1000) && main(argc, argv);
}

Another one, with a little cheating :

#include <stdio.h>
#include <boost/preprocessor.hpp>

#define ECHO_COUNT(z, n, unused) n+1
#define FORMAT_STRING(z, n, unused) "%d\n"

int main()
{
    printf(BOOST_PP_REPEAT(1000, FORMAT_STRING, ~), BOOST_PP_ENUM(LOOP_CNT, ECHO_COUNT, ~));
}

Last idea, same cheat :

#include <boost/preprocessor.hpp>
#include <iostream>

int main()
{
#define ECHO_COUNT(z, n, unused) BOOST_PP_STRINGIZE(BOOST_PP_INC(n))"\n"
    std::cout << BOOST_PP_REPEAT(1000, ECHO_COUNT, ~) << std::endl;
}