He played at slower tempos with a large pick that was easier to hold . In 2006 , at the age of 90 , he won two Grammy Awards at the 48th Annual Grammy Awards for his album '' Les Paul & Friends : American Made World Played '' . He also performed every Monday night with guitarist Lou Pallo , bassist Paul Nowinski ( and later , Nicki Parrott ) , and guitarist Frank Vignola and for a few years , pianist John Colaianni . Paul , Pallo , and Nowinski performed at Fat Tuesdays and at the Iridium Jazz Club on Broadway . In 1997 , Chuck Mangione did a session with Les Paul . Mangione is told of how he beat out Les for Album of the Year
48th Annual Grammy Awards
48th Annual Grammy Awards
Les Paul