Kenny was born in New York City in 1958. He started music lessons at the age of four. After studying classical piano with his Aunt Marjorie, he branched out into the area of jazz music.
Kenny Jr. has performed worldwide with a comprehensive variety of musicians, including Stanley Jordan, Out of the Blue (OTB), Stanley Turrentine, Slide Hampton and the Jazz Masters, the Mingus Big Band, Steve Grossman, Yoshiaki Masuo, Sadao Watanabe, Smokey Robinson, Frank Morgan, Daniel Schnyder, and many others.
Kenny Drew Jr. was the winner of the 1990 Great American jazz Piano Competition in Jacksonville FL. He has appeared as a leader at many major festivals, including the Jacksonville Jazz Festival, Kyoto Jazz Festival, Savannah on Stage Festival, Clearwater Jazz Festival, and the Newark Jazz Festival.
Kenny has also performed as leader at many major jazz clubs around the country, such as Bradley's (NY), Visiones (NY), The Blue Note (NY), Blues Alley (DC), Fat Tuesday's (NY), The VIllage Gate (NY), Trumpets (NJ), The Jazz Showcase (Chicago), Twins Lounge (DC), One Step Down (DC), and the Montreal Bistro (Toronto).
He has recorded nine albums as a leader and has also made numerous recordings as a sideman.