Back when I sang at a lot of karaoke clubs, I usually picked songs that I knew were easily within my natural vocal range. I'd say I was a baritone/tenor, along the lines of Elvis or Raul Malo. After a while I decided I needed to stretch my vocal range, so I started picking out songs by tenors like Roy Orbison and Paul McCartney. I crashed and burned a lot trying to hit those really high notes in songs like "Crying" and "Oh Darling". It took a few months before I could get under those big notes and hit them correctly.