5
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What are software options that will tell you where you've gone out of tune in the performance of a given song? Better if it can work with any song file or has a wealth of community-content.

Sort of karaoke-like software solutions that will help you analyse and improve your singing ability.

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1
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One way I found to achieve this is to use Carry-A-Tune Singing Coach Unlimited software. Singing Coach’s Pitch Tracking Line displays what note you are singing and the note you are supposed to be singing on a musical graph. It plays the accompanying track and a guide line on what pitch you need to be at. Then I use Guitar Pro to get songs with vocals tracks in it, export it to midi and import the same midi to Carry a Tune. This way you can learn to sing any song.

0
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I've used Starmaker for iPhone and it is similar, but you can only use the songs they have available. But the app is free and it is fun. I think the Smule app Sing! Is similar as well.

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