This achievement is best earned while grinding the 720,000xp needed to rank up the dog to level 6. After you choose your character, the next screen is where you select your "gig". At first, only the 1st one will be unlocked for each character. Eventually, after around 450,000 - 500,000xp (I think), you'll unlock the 5th and final "gig". You must play this 10 times consecutively without failing, quiting out or powering off your console. Depending on the songs chosen this should take around 4 hours.