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I spend way too much time thinking about what song to choose, but usually I just end up singing the ones I feel like doing in the moment. Everywhere by Michelle Branch is the song that I've found that has that good sweet spot of widest appeal with all ages and audience impact. I also think Since You Been Gone by Kelly Clarkson is a really good crowd pleaser. And fuck it, Mr. Brightside is never not catchy. My last one was Zombie by The Cranberries, which went lukewarm, because yeah, it was too obscure and was more sway.