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Isn't the idea for graduation to remember the time you had in school? Meaning, choose recent songs that most likely were popular or well liked that were released when y'all were still in school. I always think its incredibly sappy to choose songs that very few people are familiar with (remember, in High School, people only have ~15 years of music to base their tastes on)
Its fairly safe to say that while a Frank Sinatra tune would be relevant, it sure as heck isn't going to strike a chord with the viewer/watchers.
I can't suggest any songs, as I've been pretty detached from top40/alt-rock for the past year.
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