Taylor Bickett - Quarter Life Crisis
While not exactly a breakout smash, the song has 571,000 plays on Youtube.
The Trashcan Sinatras - Obscurity Knocks
Again, not exactly a breakout smash from 1990, but for some reason it took a long time for the video for this song to be put on Youtube and the combined audio play on Youtube is also around 571,000.
Both songs are about the challenges of youth and becoming who you want to be. The Taylor Bickett song is earnest while The Trashcan Sinatras song is caustic and ironic. Taylor Bickett is American while the Trash Can Sinatras are Scottish which might explain some of their love of wordplay.
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