Here is the quickest way to get the achievements. First play enough songs until you have enough money to watch "No More Dead" at the garage (it is the shortest song). Once you have learned this song keep on playing it at the garage until you have 500 dollars and at least 100 people (you only have to play one song and you still earn the same amount of money and fans) . This ensures that you can continue playing at the bar. Keep playing at the bar until you get the earn $5000 dollar achievement. Then you will have enough money to play and learn the rest of the songs for the other achievement. Hope this helps
Even till this day this game is still amazing, it is functional as heck and it is a lot better than what these game developers are putting out today. They need to take notes
 "Punk-o-matic 2"){kind=icon}
 "Bloons TD 5"){kind=icon}
 "Turbo Town"){kind=icon}
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