If you find Expert to be a difficult task, here are 6 songs I found using the Party Pass in the Song Catalog that are labeled as a difficulty of 1 / 5. These are the only difficulty 1 songs that are available as of 11/26/2015 in the entire catalog:
Believer by American Authors
Best Day of My Life by American Authors
Bitter Rivals by Sleigh Bells
Famous by Charli XCX
Rimbaud Eyes by Dum Dum Girls
Time to Pretend by MGMT
If you are capable of getting 5 stars on any of these songs on Expert difficulty, you can simply repeat the same song 9 more times and the trophy will pop.