Harry Connick Jr. in 1990
After leaving his hometown of New Orleans at the age of 18, Harry Connick Jr. quickly found success after signing with Columbia Records. He released his first album in 1987 and went on to provide the soundtrack for When Harry Met Sally just two years later.
In January 1990, Harry landed a spot as a musical guest on Season 15 of Saturday Night Live. The photos shown here, taken as a promo for the episode, features 22-year-old Harry in an oversized sweatshirt, ill-fitting jeans, and a 90210-inspired haircut. (Don’t even get us started on that hat!)
Thank God Jill Goodacre came along and whipped him into shape!