1. An apparatus for classifying, comparing and ordering digital files, said apparatus comprising: at least one processor; at least one memory including a computer program code, wherein the at least one memory and computer program code are configured to, with the at least one processor, cause the apparatus to perform a method comprising: classifying each digital file of a plurality of digital files according to a plurality of metadata characteristics associated with, and describing musical characteristics of, the digital file, wherein the digital file is representative of a song track or other musical content; generating, in association with the plurality of digital files, a plurality of similarity scores, wherein each similarity score of the plurality of similarity scores between one digital file and other digital file of the plurality of digital files, is an aggregation of a plurality of weight scores corresponding to the plurality of metadata characteristics, wherein generating the similarity score between the one digital file and the other digital file includes: for each metadata characteristic of the plurality of metadata characteristics associated with the one digital file and the other digital file, determining a range and a weight associated with the metadata characteristic, comparing a first value of the metadata characteristic associated with the one digital file, with a second value of the metadata characteristic associated with the other digital file, and upon determining that a difference between the first value and the second value is within the range associated with the metadata characteristic, associating a match value with the metadata characteristic, and applying the weight to the match value associated with the metadata characteristics to determine a weight score for the metadata characteristic; and aggregating determined weight scores corresponding to the plurality of metadata characteristics to generate the similarity score between the one digital file and the other digital file; subsequent to generating the plurality of similarity scores for the plurality of digital files, determining a path associated with the plurality of digital files, based on the plurality of similarity scores for the plurality of digital files; and generating a playlist that includes a selection of the plurality of the digital files ordered in accordance with the determined path.