For those of you out there that are a part of today’s generation, a Sony Walkman is the 1980’s version of an iPod, only it has no GB’s and instead plays compact cassette tapes, and ran off of replaceable batteries.
Em is saying that he will always be fine as long as he has his music with him, which is something many of his listeners can relate to.
The walkman enforces the image of the passage of time with each. The first verse recalls his schooling days. The second is during his up-and-coming rapper and his career. In the third, he refers to a lot of recent events.
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