Holidays with Harry and his 2008 release, What A Night! A Christmas Album. Harry Connick, Jr. is an accomplished singer, pianist, and actor who emerged in the late 1980s as a Sinatra-style crooner for a new generation. As a musician, his influences include Bebop, New Orleans Jazz, and big-band swing. His score for the film When Harry Met Sally brought him national acclaim and an Oscar. He has appeared in many films and he is known for his Pop music as well.