#10 “The Great Beyond” by R.E.M.

Next to Genesis, R.E.M. is my favorite band of all time. Choosing one song is really hard, but “The Great Beyond” is the one that hits me in the gut the hardest. From the movie Man on the Moon, this song manages to relate specifically to Andy Kaufman and yet apply to any artist whose ever struggled to say something profound.

#9 “Hallelujah” by Rufus Wainwright
I’ve heard this song covered many times, but I’ve never heard a version as achingly beautiful as this one by Rufus Wainwright. Its so simple, just a voice and a piano, and yet it conveys more than any symphony could.

#8 “Mrs. Robinson” by Simon & Garfunkel

The Graduate is the best soundtrack ever recorded for a motion picture. Don’t argue with me, you’re wrong! Despite it being very much a product of the 60s, I completely relate to this song on every level. It is one of the most clever, brilliant pieces of work in all music.

#7 “Son of a Preacher Man” by Joan Osborne
I love the Dusty Springfield original, but this cover is just so down and dirty. The biggest regret I have over not being fabulously gay is that I’ll never be able to sing this song in a drag show. Seriously, where are the gay covers of this song!? That would be so awesome.

#6 “One For My Baby” by Frank Sinatra

This list is very rock heavy, but I love all kinds of music, and have a real affection for old crooners like Sinatra. This is such an amazing song, so filled with regret and loss. I’ve made it clear that I want this song played at my funeral.

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