Harry Connick, Jr., was born Joseph Harry Fowler Connick in New Orleans, Louisiana, on September 11, 1967. His father, Harry Connick, Sr., was of Irish Catholic descent and the district attorney of New Orleans for 27 years; his New York-born Jewish mother was a Lousiana Supreme Court Justice. His parents also owned a record store. Connick's musical talents soon came to the fore when he learned the keyboards at the age of three, played publicly at six and recorded with a local jazz band at 10. His musical talents were developed at the New Orleans Center for the Creative Arts and under the tutelage of Ellis Marsalis and James Booker. Connick attended Jesuit High School in New Orleans. He moved to New York City to study at Hunter College and the Manhattan School of Music, where a Columbia Records executive persuaded him to sign with that label. His first record, Harry Connick Jr., was a mainly instrumental album of standards. He soon acquired a reputation in jazz due to extended stays at high-profile New York venues. His second 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..., starring Meg Ryan and Billy Crystal. The soundtrack consisted of several standards, including "It Had to Be You", "Let's Call the Whole Thing Off" and "Don't Get Around Much Anymore", and achieved double-platinum status in the United States. He won his first Grammy for Best Jazz Male Vocal Performance for his work on the soundtrack. Connick made his screen debut in Memphis Belle (1990), about a B-17 bomber crew in World War II. In that year, he began a two-year world tour. Not content with that, he released two albums in July 1990: the jazz trio album Lofty's Roach Souffle and another album of standards titled We Are in Love, which also went double platinum. We Are in Love earned him his second consecutive Grammy for Best Jazz Male Vocal. "Promise Me You'll Remember", his contribution to the Godfather III soundtrack, was nominated for both an Academy Award and a Golden Globe in 1991. In a year of recognition, he was also nominated for an Emmy for Best Performance in a Variety Special for his PBS special Swingin' Out Live, which was also released as a video. In October 1991, he released his third consecutive multi-platinum album, Blue Light, Red Light, on which he wrote and arranged the songs. In October 1991, he starred in Little Man Tate, directed by Jodie Foster, playing the friend of a child prodigy who goes to college. Harry Connick, Jr., was arrested in 1992 and charged with having a 9mm pistol in his possession at JFK International Airport. After spending a day in jail, he agreed to make a public-service television commercial warning against breaking gun laws. The court agreed to drop all charges if Connick stayed out of trouble for six months. In November 1992, Connick released 25, a solo piano collection of standards that again went platinum. He also re-released the album Eleven. Harry Connick, Jr., contributed "A Wink and a Smile" to the Sleepless in Seattle soundtrack, released in 1993. His multi-platinum album of holiday songs, When My Heart Finds Christmas, was the best-selling Christmas album in 1993.