This strips off the last directory if more than one directory in path:
foreach my $path (<DATA>) {
    chomp($path);
    $path =~ s{(?<=[^/])/[^/]+/?$}{}xms;
    print $path . "\n";
}

__DATA__
/rootdir/sub funky ---doodash/la la la/Proposal for Buttering My Feet
/rootdir/sub1/sub2/sub3/sub4/
/rootdir/sub1/sub2/sub3/sub4/file/
/rootdir/
/

[download]
Hope this helps

In reply to Re: Regular Expression Help by ercparker
in thread Regular Expression Help by Anonymous Monk

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