Connick's started learning the keyboards at the age of three, played publicly at age six and recorded with a local jazz band at ten. When he was nine years old, he performed the Piano Concerto No. 3 Opus 37 of Beethoven with the New Orleans Symphony Orchestra (now the Louisiana Philharmonic) and later played a duet with Eubie Blake at the Royal Orleans Esplanade Lounge in New Orleans. The song was "I'm Just Wild About Harry."
Following an unsuccessful attempt to study jazz academically, and having given recitals in the classical and jazz piano programs at Loyola University, Connick moved to the 92nd Street YMHA in New York City to study at Hunter College and the prestigious Manhattan School of Music, where a Columbia Records executive persuaded him to sign with that label. His first record for the label, Harry Connick Jr., was a mainly instrumental album of standards. He soon acquired a reputation in jazz because of extended stays at high-profile New York venues. His next album, 20, featured his vocals and added to this reputation.
With Connick's growing reputation, director Rob Reiner asked him to provide a soundtrack for his 1989 romantic comedy "When Harry Met Sally." He won his first Grammy for Best Jazz Male Vocal Performance for his work on the soundtrack.
New Orleans Area Habitat for Humanity, working with Connick and Branford Marsalis announced December 6, 2005, plans for a Musicians' Village in New Orleans. The Musicians' Village includes Habitat-constructed homes, with an Ellis Marsalis Center for Music, as the area's centerpiece. The Habitat-built homes provide musicians, and anyone else who qualifies, the opportunity to buy decent, affordable housing.