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What's a good way to start singing along with playing? I'm not a "natural" at guitar playing, so it seems to be that much more difficult to add vocals... :hmm
That's the ticket. It's not as hard as it may seem. On a practical level, start w/a simple song in 4/4 & just strum on the beat as you sing. The more you do that, the better you get. Little by little you will be able to add complexity to your rhythm.
Yep, practice, practice, practice. I used to think singing was the scariest thing ever, and that I'd never be any good at it. Now I sing at least 50% of the songs with my band, and receive way more attention for my singing that I do my guitar playing. Sometimes, if I have a buddy in the crowd, I'll turn the guitar over to him, and just sing, but that does feel funny, just standing there while the solos are happening.
The most important things (IMHO)
1. Know your range on the guitar neck
2. Develop your pitch really well
3. Keep it simple at first, then as time goes by add vocal inflections, etc.
4. Learn the lyrics, really well (I still have issues with this)
5. Stick to songs that have the same rhythm on guitar as the vocals do, like Chuck Berry stuff, etc.
If you have good pitch, you'll be doing well in no time flat, if you figure out how to work a crowd, then you'll really have life by the balls.