Wonderful little program.

I couldn't help myself from noticing though you can combine your two loops in addWord if you randomize the order you brute force search. As long as your brute force search hits all possibilities, you can search in whatever order you want.

sub randomizeArray(@)
{
    my @array = @_;
    for my $i ( 1 .. $#array ) {
        my $j = int rand( $i + 1 );
        ( $array[$i], $array[$j] ) = ( $array[$j], $array[$i] );
    }
    return @array;
} ## end sub randomizeArray(@)

sub addWord
{
    my ( $grid, $word ) = @_;

    for my $dir ( randomizeArray( 0 .. 7 ) ) {
        for my $y ( randomizeArray( 0 .. $height - 1 ) ) {
            for my $x ( randomizeArray( 0 .. $width - 1 ) ) {
                if ( wordFits( $grid, $word, $x, $y, $dir ) ) {
                    insertWord( $grid, $word, $x, $y, $dir );
                    return 1;
                }
            }
        } ## end for my $y ( randomizeArray...
    } ## end for my $dir ( randomizeArray...

    return 0;
} ## end sub addWord
[download]

It would also be neat if you allowed for 'turns' when adding a word. ex. in a 2,2 grid allow the word 'perl' as

pe
rl

I think the game 'boggle' allows for word grids in this style.