I've heard this song dozens of times. I suppose I've enjoyed a bit of Schadenfreude in the listening, but something about it always disturbed me.
Today, it came to me. Skipper Dan isn't a victim to be pitied. He's a pussy.
Here's the deal: You give up, you lose. If Skipper Dan has really given up, I feel contempt for him.
But here's the real kicker: You make the best of where you are. In Skipper Dan's case, he has a crappy job boating tourists around in a circle. Dozens of times a day, telling the same lame jokes. Well, here's a joke for you, listen to Denis Leary's "No Cure For Cancer".
He covers it best when he explains "Shut the F*** up! You're not happy? Life didn't turn out like you expected? Hey! I thought I was gonna be the starting center fielder for the Boston Red Socks! Life sucks, buy a helmet."
What Skipper Dan needs to do is just enjoy the moment. Seriously. Those pasty white tourists from Duluth and Buffalo want to have a good time. They paid their money, but you owe them. This may be their only time in The Magic Kingdom. Make it fun. They are people, just like you. Live vicariously, and laugh. God puts us where we are for a reason. If we must serve others, don't do so with a heavy heart. Don't act like you enjoy life. ENJOY LIFE!
At one point in the song, Skipper Dan laments that he's "...laughing but crying inside..". And that's where he fails. Your audience can always smell a fake. Suck it up, do your job, and just maybe you'll finally make it. In the meantime, act like you're happy to be here. Because you should be.