You need to switch to list view to reorder songs in a playlist. To switch to list view click the list view button in the upper left hand side of the top of the iTunes windows: ![List view][1] Once you've switch to list view you can drag tracks around in the playlist to reorder them. For example, I switch Planet Earth and The Valley in the playlist shown above by clicking on Planet Earth and dragging it up above The Valley and then releasing my mouse button: ![Switched songs][2] [1]: https://i.sstatic.net/wnM5x.png [2]: https://i.sstatic.net/3D9fj.png