I noticed the specificaition for Collections.sort:
public static void sort(List list, Comparator super T> c)
Why
It's obvious to you that, in the case of Comparator, any ancestor of T would work. But the compiler doesn't know that class Comparator functions like that - it just needs to be told whether it should allow <T> or <? super T>.
Viewed another way, yes it's true that any Comparator of an ancestor would work in this case - and the way the library developer says that is to use <? super T>.
There's a really nice (but twisty) explanation of this in More Fun with Wildcards.
This is similar to C#, I just learned about it a couple days ago as to why (the hard way, and then the PDC informative way).
Assume Dog extends Animal
Blah<Dog> is not the same as Blah<Animal> they have completely different type signatures even though Dog extends Animal.
For example assume a method on Blah<T>:
T Clone();
In Blah<Dog> this is Dog Clone(); while in Blah<Animal> this is Animal Clone();.
You need a way to distinguish that the compiler can say that Blah<Dog> has the same public interface of Blah<Animal> and that's what <? super T> indicates - any class used as T can be reduced to its super class in terms of Blah<? super T>.
(In C# 4.0 this would be Blah<out T> I believe.)
The simple answer to your question is that the library designer wanted to give the maximum flexibility to the user of the library; this method signature for example allows you to do something like this:
List<Integer> ints = Arrays.asList(1,2,3);
Comparator<Number> numberComparator = ...;
Collections.sort(ints, numberComparator);
Using the wildcard prevents you from being forced to use a Comparator<Integer>; the fact that the language requires a wildcard to be specified by the library designer enables him or her to either permit or restrict such use.
Josh Bloch had a talk at Google I/O this year, called Effective Java Reloaded, which you may find interesting. It talks about a mnemonic called "Pecs" (producer extends, consumer super), which explains why you use ? extends T and ? super T in your input parameters (only; never for return types), and when to use which.