Picking the Right Karaoke Song - The Fine Art

On Thursday, some friends and I headed to our local watering hole (that's a bar, to you common folk) after work.  When we walked in, we heard the plaintive, slightly off-key warble that was unmistakable.  That's right... It was Karaoke Night.

"But Dylan," you ask, "Karaoke is for losers.  How could you stand it?"  To that I can only reply that, yes, it is for losers, and I count myself as the biggest loser of them all.  I belted out three tunes that night.  I did my standard "Walking in Memphis" (not the stupid country version, but the original, complete with gospel organ), "Levon", and "Midnight Train to Georgia" (no, I was not a Pip.  When your star shines as brightly as mine, you can't squander it as a measly backup singer.  I AM Gladys Knight).

Already you are are marveling to yourselves at such amazing song choices.  Really, those are the perfect Karaoke songs.  Well, I am here to impart my wisdom to you because picking the right Karaoke song is more difficult than people realize.  It is all too easy to fall into some common traps, and I'm here to help you avoid them.

1. First thing is to get to know the crowd.  You never, EVER want to be the first person to sing.  Even the second slot is too soon.  The ideal spot for your first song is seventh, though sixth can be substituted if the crowd is especially sparse.  Here's why:  You need to gage the crowd's reactions to the songs that go before you.  If, for instance, someone gets up and sings the Dixie Chicks, and immediately there is a mass exit to the restrooms, you know that you are dealing with a more particularly urban crowd, but if they begin to two-step, then this might not be your kind of audience.  (See Rule #3).  However, if the first person up starts singing "Holla-Back Girl" (as in "I ain't no..."), and the audience goes nuts, then you know you are dealing with a younger, and slightly less sophisticated crowd.  Picking something from the sixties or seventies might not be your best bet.  Knowing what kind of crowd you are in is key to selecting a song with widespread appeal.
2. Avoid songs with long instrumentals.  This seems like a no-brainer, but you'd be amazed how many people pick "Copacabana" in an attempt to be ironic, but forget about the 2 minute long instrumental portion which leaves them naked and vulnerable on stage.  The only possible results are standing there, boring the hell out of your audience or attempting some lame lambada number.  Either way, you lose.
3. Country music is never acceptable.  Ever.  Period.  Country music is the lazy songwriter's medium, and it is incredibly easy to sing.  Unfortunately, upon your selection of a country song, you have been automatically lumped into "wants to be on American Idol and be the next Carrie Underwood" territory.  That is never good.  The rules are a little different for old school country.  Yes, we all like "Ring of Fire", and, yes, it might be satisfying to get to sing "... She got run over by a damned old train," but those songs are cliche'd.  90% of all Karaoke nights include these songs, and you don't want to be the one who does them.
4. Rap music is never acceptable.  Ever. Period.  I know that you like big butts, and I know that you are having trouble lying about it.  But no one knows the third verse to any rap song well enough to pull it off, and this will lead to only one possible outcome (See #6).
5. Overly obscure songs are not your friend, but neither are overly obvious ones.  This is a tough part, especially for those who consider themselves especially musically literate.  I'll point to my choice of the song "Levon."  The more obvious Elton John choice would have been "Tiny Dancer," but everyone knows it.  By choosing "Levon," a song that many don't know but that has a rocking hook, you get the benefit of Elton John cheesiness™ but you also appear to have a better than average knowledge of deeper album cuts.
6. Duets are fine, but group sings are not.  Picking the right duet is a science, but less so than the solo song (Basically, avoid anything from "Grease").  Group songs are nothing but audible torture for the audience, who cannot wait until the song is over.  This is because, inevitably, there is one person in the song who can sing, and the rest can't, leading to an unbearable cacophony.
7. Know your voice.  You'll notice that my three choices were all fairly similar in range and style.  This wasn't by accident.  I know that I can't sing anything by 311 or Nirvana, because my voice is more traditional (I was classically trained, you know).  So, the songs I chose are all by noted vocalists.  Knowing what kind of song fits your voice best is important. 
8. Know your song.  There is nothing more annoying to the audience and mortifying for the performer to get up on stage, only to realize that you never knew how the melody of the verses sounded.  Your performance was doomed from the start.
9. Pick a song that has a dynamic moment or two.  It can be very tempting to pick a safe song that everyone knows.  The best example is "Stand by Me," which is melodically very simple, but takes a special kind of voice to sing it well.  Simple songs are hard to do live because you have to be a born performer with a certain innate quality to your voice to pull it off (John Lennon).  This is why "Walking in Memphis is the perfect song to pick.  It has two great vocal moments. Three, I just thought of a third.  The first is "Down in the Jungle Room."  The second is "... when you haven't got a prayer" (should only be attempted if you know how to flip into your falsetto.  The third, and perhaps the greatest of all Karaoke moments is "Ma'am I am tonight."  No matter what is going on in the crowd, everyone will stop down for that moment.
10. Finally, know when to quit.  It doesn't matter how talented you are, or how much you killed on your earlier songs.  No one likes a stage hog (the only exception is if you are called up for an encore).

So, there you are.  Some simple but important rules.  Other than that, have fun with it.  Above all, don't be afraid to look a little stupid (small amounts of idiocy can actually aid a good Karaoke performance).  Please feel free to steal any of my song choices, as they have already been prescreened and selected by a master in the craft.