The thumbpick is an essential tool for all 3 finger style 5 string banjoists. The thumb is the most used finger for the picking hand and what pick you use will have a great effect on both the tone you get out of your banjo and the playability.
When choosing a thumbpick I look at 3 things:
You want your thumbpick to fit snug onto your thumb so that it doesn’t move around and fall off while you’re playing, but you don’t want it so tight that you cut the blood circulation off from the tip of your thumb.
The wrap on thumbpicks that holds the pick onto your thumb is sometimes made of plastic and other times of metal. The metal wraps on some picks allow you to bend it slightly to perfectly fit your thumb. The plastic wrapped ones are harder to do this. Some people go so far as to put the plastic picks in boiling water to make the plastic more malleable and then bend it to fit their thumb perfectly.
The size and shape of the pick part of a thumbpick can effect the way you attack the strings on your banjo. Some picks will make it easier for you to strike the strings cleanly while other picks might cause you to miss the strings some or get hung up on them. You have to experiment to see what work best for you as everyone is different.
The type of plastic used on the pick part can affect how the pick strikes through the strings. Some plastics might be smoother than others so there is less friction and the picks go through the strings easier.
The thickness or hardness of the pick also can affect how your thumb plays through the strings. A thin or softer pick might have more flex in it so when you strike the strings there is a little bit of give in the pick. It is a personal taste as to what you prefer.
Some of the aspects that was talked about under Playability will affect your tone. Different picks will have you strike the strings differently thus affecting your tone. Different plastics used with different hardness and thicknesses also affect your tone. Some will be brighter than others, some with a more rounded tone.
Experiment with a number of different thumpicks and see what works best for you. When you find something, stick to it!
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