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How to Open an iTunes Playlist in a Separate Window on a Mac

The other day I wanted to drag a new song I’d purchased at iTunes into one of my playlists. However, there seemed to be no easy way to have two iTunes windows open to do this. It may be easier when macOS Catalina debuts this fall and breaks up the iTunes app into separate Apple Music, Apple Podcasts, and Apple TV Plus apps, but for now, it’s a little convoluted (at least for an Apple product), but you can do it. With iTunes launched:

Go to your Music Library by clicking Library at the top middle of the iTunes screen.

Move your cursor to the iTunes Sidebar on the left side of the app. If the sidebar is hidden, use the keyboard shortcut Option + Command + S to make it appear.

Choose an iTunes playlist.

Right-click or Control-click on the iTunes playlist and select Open in New Window.

iTunes Playlist2

Now you can add items to the playlist, delete ‘em, or perform tasks as needed.

Dennis Sellers
the authorDennis Sellers
Contributing Author
Dennis has over 40 years of journalism experience and has written hundreds of articles. For the past 20-plus years, he's been an online journalist, covering mainly Apple Inc. He's written for MacCentral, MacWorld, MacMinute, Macsimum News, Apple Daily Report, and is now contributing editor at Apple World Today.
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  • That’s good but I have stuck with iTunes 10 which was back before they broke everything, and it Even did syncing?
    I’m glad they brought multi window back.
    I have been using mac osx 10.14 on a secondary computer (Main is 10.6) trying to cope with iTunes which is just a complete disaster for navigation, it’s almost like they purposely made it take multiple clicks to do stuff when it normally used to take one click at the most.

  • You’re still not able to edit the playlist, rearrange etc. This was a major screwup by Apple.