6. "A Summer in Ohio" by Jason Robert Brown from The Last Five Years
Part of the problem with summer is that you wait so long for it to come, but then you don't spend the entire three months on the beach with a cold drink. Unless you're a kid on break from school, there are long stretches where you have to live your life and deal with its complications. This is captured perfectly in the witty character song Jason Robert Brown wrote for the Cathy in The Last Five Years. Her attempt to manage her career in summer stock with her troubled relationship is hilarious and adorable.
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