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Album Artwork Assistant

Finds album cover artwork on the Internet and adds it to music track files in iTunes. Batch queue searches for a large number of CD covers, then processes the queue unattended.

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Bowtie

Control iTunes with shortcuts and submit songs to Last.fm. Choose from a number of beautiful themes or create your own.

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Counterpoint

In this game, several songs play at once, and as you guess their names correctly, they stop playing.

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DeTune

Plug in your iPod, launch DeTune, and get access to all your songs. Copying them to your Mac is a simple drag and drop. Other features include tweakable filename templates and preferences for a files list. DeTune is the successor to expod.

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DockArt

Plug-in turns the iTunes icon in your dock into the album art for the currently playing song.

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Ejector

Eject your iPod with a button on the menu bar.

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Encyclopodia

Install Wikipedia on your iPod for on-the-go reference, but only if you don’t mind installing Linux as well.

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Floola

Efficiently manage your iPod music, videos, podcasts and photos in one simple app, anywhere on any computer. Supports almost all features offered by iPods including photos, artwork, podcasts and smart playlists.

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Flutter

Play, pause and skip songs with simple hand gestures and your webcam. Works with iTunes, Spotify, MPlayerX (latest version) and Quicktime. Fun, yes, but usefulness questionable.

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Fountain Music

An iTunes visualizer that responds to the beat of the music in the form of a colourful water fountain. Or visualize the CD itself with JewelCase.

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GimmeSomeTune

Control iTunes from the menu bar, but cooler than that is a floating, translucent window that pops up when a song begins. Use preferences to customize it and decide how long it stays there.

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I Love Stars

Shows the rating of the song currently playing from iTunes in the menu bar. Make adjustments with your mouse or keyboard shortcuts. Alerts for unrated songs.

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iConcertCal

iTunes plug-in monitors your music library and generates a personalized calendar of upcoming concerts in your city.

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iTunes Alarm

Not only puts you to sleep and wakes you up, but does the same for your Mac. This app plays the music of your choice as you fall asleep, then puts your Mac to sleep at the time you designate. Later, it can wake your Mac and play another song (or radio station) to wake you up. There’s even a snooze button.

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iTunes Doodad

An icon in your menu bar lets you switch playlists, skip tracks, or pause iTunes, all without using the iTunes interface.

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Join Together

Join the files of selected iTunes tracks together with QuickTime and export them as a single AAC file/track. Website has plenty of other AppleScripts for iTunes to explore.

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Juice

This podcast receiver lets you capture and listen to podcasts whenever you want.

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Mashduo

Compare your iTunes library with a friend’s and see which songs you don’t have in common. Or use it to make sure your own libraries are in sync. Also helps with making sure a migration goes well.

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Quick Tag

Tag songs in iTunes for easy organization and better smart playlists.

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SizzlingKeys

Control iTunes from your keyboard without leaving the app you’re working in. Hot keys allow you to totally tune in.

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Sleepytime

Sleep timer for iTunes features an animated display showing the current song’s title and artist, as well as time remaining until the music fades out. When the music ends, you can have your Mac shut down, restart, sleep or log out. Or have Sleepytime hide or quit.

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Tooble

Browse, search, and download YouTube video directly to your iPod.

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TuneConnect

Use this nifty panel to control the tunes on one Mac with another one over a network.

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TuneLyrics

Fetches the lyrics of the song playing on iTunes. If you like them, you can click on Approve and have them added. If it can’t find the lyrics, there is an option of having Google look for them.

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YamiPod

YamiPod has a whole range of options that allow you to manage your iPod. In fact, you can run it on your iPod.

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You Control:Tunes

Have complete control over iTunes from the menu bar.

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