All credit goes to A 0 E Monkey and his guide at X360A.
This achievement will require you to use the old man. To unlock him just rank up any character to 240,000xp. Then select the old man and select superstar mode(the first selection) and play the first gig. You'll play 3 songs, then randomly select and play 2 more. After 5 songs are played, a spinner will appear with 5 spots which determines which song of your 5 you will play again. To even have a chance at the achievement, spot #5 must have the "item" on it. The achievement is to hit the #5 while the item is on it using the old man. This took me 8 straight hours, but it's completely chance so it may take 1 chance or 1000! Also, as mentioned in A 0 E Monkey's guide, NEVER quit out of any gig at any time as it may glitch this achievement. You can fail out, but NEVER quit. Once you hit 5 with the item, you'll have to play the 6th song and at the results screen (after a VERY suspenseful pause) POP! This achievement is extremely annoying so good luck!