It is advisable to snap the achievement app, so that you can see that progress is being made.
First hit your to move to Radio and select any artist and start playing a track.
For the first achievement you will need a Kinect. Just alternate between saying "Xbox pause" and "Xbox play" until you get this achievement.
Once you have that out of the way, either hold down or use an elastic band to hold it in place. This will effectively keep restarting the song, which registers as a new song. Leave it skipping back to get the next three achievements. If you can, connect your controller with a micro USB to stop it from turning off, otherwise you have to keep turning it back on from time to time.
Next, back out to the main home page. Hit until you get to the Top Music tab. Select the Top Songs menu on the left which will bring you to the Top Music screen. At the top there are a couple of drop down menus. Select the Genre menu and choose Pop. Then play any song. After a couple of seconds, go back and select a different genre and play a song. Once you have played something from each genre, you will get this achievement.
While hovering over any song from any genre, press . This will bring up a menu. Select "+Add song" and then "+New playlist". Name the playlist anything you like (for speed pick a random letter). Do this four more times for the next achievement. It can be the same song, just choose different names (letters) for the playlists.
While playing any song, move the (up). You will then find the options to turn shuffle on and turn repeat on. Toggle each of these on and off ten times until the next two achievements pop. For speed, do one first and then do the othe,r once you get your achievement.
Now you have just the grinding bit to do. Go to one of your playlists and make sure it just has a couple of songs in it. Turn on repeat and shuffle and press to start a song playing. Then, using an elastic band, hold down the (you can of course do this manually, but you will be there for some time). Then just leave it playing. It will keep skipping to the next song which will count as a song being listened to.
Credit to Itzz Sh0wt1m3 for finding this quicker method.
This will not work on radio.
You will eventually get the next two achievements, although it will take a couple of hours. Again, if you have a micro USB, use it to keep the controller on.
So, that's it. You're done. Don't forget to cancel your free trial so you don't have to pay. To do this go to Xbox.com and you will find it under Subscriptions in the profile menu (hit your gamertag in the top right to bring down the menu).
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