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Use "smart" playlists to let iTunes make playlists for you. Set the parameters for your playlist. Click the "+" button to add new parameters. Click the ". Make sure the "Match The Following Rule" box is checked. Check "live updating" to keep your playlist automatically up to date. Alternatively, make Genius Playlists to find similar songs automatically.

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Smart Playlists allow you to give iTunes a set of parameters to make a playlist for you. For example, I could create a smart playlist that organizes all of my recent music label "rock," and iTunes would find all of the songs for me. To make one, click on the "Playlists" header at the top of iTunes, click on the small gray cross in the bottom left corner, then choose "New Smart Playlist." Smart playlists can make a list of all the music you've added that month, every one of your top rated "jazz" songs, only songs with high quality audio, your most played songs, and more. The smart playlist window allows you to tell iTunes where to find the music you want. From here, you can choose the parameters for your playlist:  The first box chooses how to organize you playlist (album, artist, genre, file size, etc.) The second box defines the parameter, (contains the phrase, is not, etc) The third box let's you input what songs you want to choose from. For example, if I want a playlist of all songs by "The Who," I would select "Artist" in the first box, "Contains" in the second, and then write "The Who" in the third. This means the playlist will contain all songs by the artist, "The Who." This lets you chose songs by genres, plays, date added, bit rate -- you name it. You can make as many parameters as you'd like and iTunes automatically sorts your songs. .." button to adjust parameters. For example, if you want to add The Who, but don't want any of the songs off of the album "Tommy," you can click "..." and choose "Album," "Does Not Contain" and write in "Tommy." Otherwise the playlist will just choose random songs. This is useful if you choose parameters like "recently added songs" or constantly download new music. Every time you open iTunes it will update the playlist for you. iTunes can take almost any song and find 20-30 songs like it, making a playlist for you. To make a Genius Playlist, right click on a song and select "Create Genius Playlist." You can then add or delete songs from this playlist like any other.