Clickwill

How to manage songs on an iPod classic

The iPod classic can't edit its own library, and Apple's sync only copies what's in the Music app. Clickwill opens the library on the iPod itself, so you fix songs and albums right where they are.

Short answer

Connect the iPod and open Clickwill. Find, rename or delete songs in Songs, open an album from Cover Flow to reorder its songs, and use Edit for the cover, album name and year. Every change waits until you click 1 change pending and Write to iPod.

Find any song

  1. Click Songs in the sidebar

    It lists every song on the iPod with its artist, album, play count and length.

  2. Search, sort or play

    Type in the search field at the top right. Click a column title to sort by it. Double-click a song to play it from the iPod.

    The Songs table in Clickwill searched for Ozzy, with title, artist, album, plays and time
  3. Right-click a song to change it

    Choose Edit Title… to change its title or track number, Show Album to open its album, or Delete from iPod. To delete several songs, select them first.

    Editing Goodbye to Romance from the Songs table: title and track number, with Cancel and Save

Rename a song from its album

  1. Open the album

    Double-click its cover in Cover Flow.

  2. Choose Edit Title

    Right-click the song, or click ··· at the end of its row, and choose Edit Title.

    The menu of a song: Play, Edit Title, Edit Track Number, Renumber Tracks, Replace Audio File, Delete from iPod
  3. Type the new title

    Press Return to keep it, or Escape to leave the title as it was.

Change the cover, album name or year

  1. Open the Edit panel

    In the album, click ··· next to Play and choose Edit.

  2. Change what you need

    The panel has the cover, album name, album artist, year and genre. Click the cover to choose a new image, or drag one onto it. These fields apply to every song in the album.

    The Edit panel of Blizzard of Ozz: cover, album, album artist, year, genre, number of songs and position on the iPod

Put songs in order

In the album, drag a song up or down the list. The iPod plays the album in that order.

Put albums in order

  1. Open Reorder Albums

    In Albums, click the ↑↓ button at the top right of the window.

  2. Drag albums into place

    Drag an album within its artist, or move a whole artist with the arrows next to the artist's name. The list on the right shows the iPod's Albums menu as it will look.

    Reorder Albums with albums grouped by artist and a preview of the iPod's Albums menu on the right
  3. Click Done

    It's at the top right.

Delete a song or an album

  1. Choose what to delete

    For a song, right-click it and choose Delete from iPod. For a whole album, click ··· next to Play and choose Delete Album….

    The album menu with Add Songs to This Album and Delete Album
  2. Keep a copy if you want one

    Clickwill asks first. Save Copies and Delete… keeps the files on your Mac, Delete removes them from the iPod for good. A backup of the iPod's library is taken before every write, but it doesn't hold the music itself.

    Delete Blizzard of Ozz? with Save Copies and Delete, Delete and Cancel

Put your changes on the iPod

  1. Click 1 change pending

    It's at the bottom of the window and counts everything you've changed so far.

  2. Click Write to iPod

    Check the list first. Clickwill takes a fresh backup of the iPod's library, writes your changes and checks them. If you change your mind later, Backups in the sidebar can put an earlier library back.

    Pending changes: rename Crazy Train to Crazy Train (Remastered), with Discard All, Close and Write to iPod
Download Clickwill Free alpha for macOS 26 or later.