Create a "Block Party!" playlist containing random Artists and a specific number of their randomly selected songs arranged in a row ("two-fers"three-fers", and so on), one block of tracks per artist without artist repeats. You can restrict the size of the "Block Party!" playlist by Number of Artists or Duration in hours. Additionally, you can choose to use a particular Playlist as the source of tracks and restrict various Genres.
For iTunes 11 and later, OS X 10.8 or later.
Main window and settings.
(via in-app purchase)
Perhaps Also of Interest...
downloaded 13m 30s ago
Delete characters from the beginning or ending of selected tracks' name, artist, album, comments, composer, or show tags
downloaded 14m 33s ago
Copy number prefix in Song Name of selected tracks to their track number tag
downloaded 16m 33s ago
Remove iTunes tracks disassociated from files
downloaded 46m 3s ago
Exports and then re-imports selected tracks' artwork
downloaded 1h 13m 13s ago
View/Edit tags of selected track(s) in single window
downloaded 1h 24m 14s ago
Applet compels you to rate unrated current track