Best singer playing the uke.

UkingViking

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Lisa Hannigan deserves a mention. Not strictly an ukulele player, plays more guitar, but often seen with her MyaMoe:

 

Brad Bordessa

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Raiatea is just a stunning singer. I haven't heard anybody else who plays uke who ever struck me as even coming close in power, control, and proficiency - male or female (except maybe Willie K, but he mostly played guitar). I've seen her live a number of times and it's always been top-notch, world class. Really one of the best in the business and probably doesn't get enough credit.
 

donboody

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Mark Yamanaka

ok I just realized I probaby disqualified myself because he isn't playing a uke there, but his voice is incredible and he does play uke a lot and here he is doing it and sounding just as incredible

 
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man0a

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RIP Uncle Willie K. He could play and sing rock-and-roll, blues, opera, folk music (from different countries), reggae, traditional Hawaiian music, and medleys combining different styles. His live shows were always fantastic.
 

Voran

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Nautiloid. She is amazing.

nautiloid.bandcamp.cpm
 

badhabits

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What about Kelly boy Delima? If you're in Waikiki, he plays fo free most Thursday nights at the Surfjack.
 

Bill Sheehan

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He may not have a lot of ukulele chops, but Lordie I love his voice!
You bet! Great voice indeed! Reminds me just a little bit of my longtime idol, Terry Kath (Chicago's original guitarist, now deceased, who sang such songs as "Make Me Smile" and "Colour My World").