Do you have to sing along with a mic or is there a button on the control to press?
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I don't know if singing in the mic counts but if you change the radio station until you find the song "take on me" by AH-HA your caracter will start to sing along. And yes I did sing along thats when I got the achievement.
Your character will sing.
I have no idea how I got it. I got out of my car and got the acheivement, so I can only assume my guy was singing beforehand.
But all my friends and others who I have spoken to say it's songs on the 80's music station that activates it. I think you might have to listen to one station for a long time or something.
Just go to the music store and buy it save it to your palylist then go to it and just wait for it
If you put "The Final Countdown" as the only song in your playlist and you play in from the very beginning you will automatically sing along it works better in your car
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