This began a period of top ten hits including "Music Makers" and "Lament To Love", which featured his new vocalist, Dick Haymes. Following, was the classic "You Made Me Love You", which became his biggest hit at that time, but is also the tune that jazz purists most hate. From then on, it was hit after hit as Harry and his band reached star status. Songs such as "It's Been A Long, Long Time", featuring vocalist Kitty Kallen, "Sleepy Lagoon" and "Ciribiribin" were big sellers for him.

He also began appearing in movie musicals — as did many bandleaders — and in 1943 married Grable, with whom he'd co-starred in Springtime In The Rockies. He worked extensively in films while continuing to lead his band and issue recordings, but as the war ended there was a decline in the popularity of the big bands. Eventually he dissolved his group, but within a year or two decided to try it again, and was fairly successful. He also moved back closer to his original jazz roots, leaving behind the schmaltzy sound that so irritated the pros.

During the 1950s he continued actively working, recording with a number of singers, including Frank Sinatra, and even had his own TV show for a while. He was also said to be the inspiration for the Kirk Douglas film Young Man With A Horn, for which Harry provided the sounds emanating from Kirk's trumpet. He also played himself in the 1955 movie The Benny Goodman Story, which included a recreation of that famous Carnegie Hall concert.

Harry inevitably slowed down through the years but always continued performing as much as possible, until the early 1980s and his death at age 67 from lymphatic cancer. He was a talented performer, probably one of the best-remembered of the trumpeters, and hopefully has by now been forgiven for straying into commercialism for many years. After all, a guy's gotta make a living.