1,000 iterations isn't remotely generous for JRuby, unfortunately - JVM's Tier-3 compilation only kicks in by default around 2,000, and full tier-4 is only considered beyond 15,000. I've observed this to have quite a substantial effect, for instance bringing manticore (JRuby wrapper for Apache's Java HttpClient) down from merely "okay" performance after 10,000 requests to pretty much matching the curb C extension under MRI after 20,000.
You can tweak it to be more aggressive, but I guess this puts more pressure on the compiler threads and their memory use, while reducing the run-time profiling data they use to optimize most effectively. It perhaps also risks more churn from deoptimization. I kind of felt like I'd be better off trying to formalise the warmup process.
It's rather a shame that all this warmup work is one-shot. It would be far less obnoxious if it could be preserved across runs - I believe some alternative Java runtimes support something like that, though given JRuby's got its own JIT targetting Java bytecode I dare say it would require work there as well.