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If you want a fun karaoke night, first song(s) need to be something that will get most everyone singing. Younger crowds: something like Tayor Swift "Shake It Off". Middle age crowds, something like Nirvana or Aerosmith. Older crowds any Beatles #1.
I personally like Cyprus Hill "Jump Around" if you're willing to learn it well enough beforehand as to not butcher the lyrics. I've seen Vanilla "Ice Ice Baby" also get a similar reaction of everyone knowing the song and enjoying it enough to give you kudos for choosing it.
After everyone's over the initial hesitation, go belt all your love songs and power ballads; but get the party started first.