
A process that musicians go through in their musical evolution is '
finding their own voice'. Years are spent honing the craft and learning how to play. One aspect of this journey is establishing the actual tonal qualities - the sound - that you like best.
Guitar players today have a vast array of tonal tools to choose from. A massive selection of different guitars, hundreds of different amplifiers for both acoustic and electric guitars, and a potentially uncountable number of electronic signal processors could all come into play to sculpt different instrumental tones.
In my own path through this maze, I have thankfully settled on several guitars, all of which I have owned for 15 years or more. I spent lots of time and money on electronic signal processing, ranging from rack mounted digital devices to conventional stomp boxes, and finally decided to simplify. Less Is More. I felt that my individual voice should be heard with a good guitar, a healthy cable, an amplifier with a bit of reverb and lots of practice. This worked out well musically, and led to a new area of tonal experimentation - the Guitar Pick.
Many years ago, my cousin - the excellent guitar player from NYC Larry Dunn - introduced me to the Jim Dunlop Jazz III guitar pick. I had been playing with full size Fender Heavy picks, so this was my first experience with the Jazz Teardrop Shape, which is a smaller pick. I soon found that my picking was much more accurate and comfortable for the jazz oriented lines and comping (rhythm) styles of music I was playing full time.

After several years of comfortable playing with the Jazz III's, Jim Dunlop came out with the
Jazztone series, introducing a new texture, modified shape and new thicknesses. This is one of the best jazz picks out there. The beveled edge and texture of the material provide almost no pick noise on the string, and the pick is extremely light and comfortable to hold. I settled on the 205 model (2.00m thick), and lived happily ever after for at least 5 years of playing exclusively with this pick.
Then one day out of the blue, I thought it might be fun to experiment with different guitar picks.

After discovering that guitarist
Jimmy Bruno uses the
D'Andrea Pro Plec (1.5mm thick), I went out and got two different models. These picks cost $1.00 apiece which was an unheard of amount for a guitar pick (read on - it gets much worse!) They are made from the same material as the Fender guitar picks - fake Tortoise shell. Very comfortable, very stiff, smooth string attack; an excellent pick all around. The modified square Pro Plec is a nice option for comfortable holding.
Recently, Jim Dunlop announced a new pick to their Jazz III series - the Jazz III Ultex (1.5mm thick). This pick was made out of a different material from the original Jazz III's, which is stiffer and a little crisper. This is a good pick that I like better than the original red or black Jazz III, but not as much as the Jazztone 205.
Then came trouble. I discovered the world of hand made custom picks. I read about and decided to try a Wegen Twin pick (3.5mm thick). At $10.00 apiece, it felt like I should have been calling a Friend before placing the order, but ultimately I had to find out what a $10.00 pick played like. I'm happy to report that this is an excellent pick. It has a ribbed indent making the Twin extremely comfortable to hold. It has great stiffness and a nice beveled edge producing a soft but accurate attack on the strings.
Next I found the Jazz Stubby Surfpick (about 1.5mm thick). This pick is unusual in that it is made out of Lignum Vitae wood. This was another $10.00 guitar pick, but now I was hooked and had to have something to compare the Wegen pick to. Besides - it came in it's own really cool ring-like pick box. The Surfpick has great stiffness, but is a bit slippery to hold and has a slightly harsh, raspy sound on the strings. It is possible that that would go away with increased playing, which does nicely wear down the edge over time.

Now we arrive at my current favorite pick - the
V-Pick Small Pointed made by Vinnie Smith in Modesto, California. I like the Small Pointed Pick (at 2.75mm thick). This is one excellent pick. It's extremely comfortable to hold. As you play, the warmth from your fingers makes it stick slightly, resulting in a more relaxed grip. Because it is a thick acrylic pick, it is the stiffest of all the picks I've mentioned so far. The beveled edge produces a tone soft enough for jazz, yet with a small amount of 'chirp' or 'bite' that can be great for harmonics or percussive accenting. It comes in clear, red and glow-in-the-dark. And, at '
only' $4.00 ($5.00 for the glow-in-the-dark), it is a bargain compared to the Wegen or the Surfpick!

These are picks that I tried and rejected fairly quickly. The
Jim Dunlop Tortex teardrop series picks tend to be a bit too flappy and raspy in their sound. The
Jim Dunlop Stubby (made of 2.00 mm thick acrylic like the V-Pick) ended up having a really harsh, sharp sound that I didn't like at all. The
Clayton, while nicely thick (1.9mm) with good stiffness, for some reason feels like running through sand while playing.
Some of the picks mentioned here come in different models and thicknesses, so even if you don't like the smaller teardrop shape, there might be an alternate shaped pick available.
Try visiting your local music store, and choose a bunch of different picks. You might well discover something you like better than the pick you are currently using!
Resources
Jim Dunlop Website
D'Andrea Picks
Michael Wegen's Website
Surfpick
V-Picks
Elderly Instruments Pick Pages