What I do is sort the directories and files by size and go largest to smallest. Based on the likely distribution of files sizes, 20% of your files and/or directories will account for 80% of the hard drive space. I usually then choose candidates for deletion and evaluate them, deleting them on the spot or skipping them for this time. I do this until I get the space reduction I want or until I'm sure that I want to keep what is in the largest 20%. After I reach one of the two states: top 20% of files/directories are keepers or I deleted down X GB. This method can be done with any sorting method. For example, by play count or by date added, old to new. Keep going until the top 20% are keepers. The same distribution is likely to apply across all vertical data labels so the filter is generically usable in lots of situations. For example, 20% of car drivers likely get 80% of speeding tickets. We could reduce speeding by 80% by speed limiting these drivers' cars or by revoking their drivers licenses. Another example is memory hogs in a computer system. The top 20% of memory hogging programs likely account for 80% of used memory in a system. This distribution is called the Pareto principle. The principle is an example of a power law.