@array = qw( hello, superduper, hi )

Maybe it's a mistake, but this creates a list containing three comma ending strings.

For your algorithm you should have a look at the implementation of minmax in List::MoreUtils. It should be simple to adjust it to check for the length of a string. The documentation says:

The minmax algorithm differs from a naive iteration over the list where each element is compared to two values being the so far calculated min and max value in that it only requires 3n/2 - 2 comparisons. Thus it is the most efficient possible algorithm.

--Frank