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Glenn Miller and his band appeared in two Hollywood films, Sun Valley Serenade (1941) and Orchestra Wives (1942), the latter featuring future television legend Jackie Gleason as the group's fictitious bassist. "A stickler for the truth, insisted on a throughly believable script before he'd go before Twentieth-Century Fox cameras. And keen businessman that he was, he demanded that the band become an integral part of the story and not just be thrown into some inconsequential scene . He had achieved star status and he was now demanding and getting star treatment."

Since he went missing December 15, 1944 there have been over sixty years of theories about what happened to Glenn Miller. Buddy DeFranco, one of the leaders of the post war Glenn Miller orchestra explained to George Simon, that at many of the concerts where he was leading the Glenn Miller band in the nineteen-seventies, more than a few people confided to him what "really" happened to Glenn Miller. "If I were to believe all those stories, there would have been about twelve thousand four hundred and fifty eight people there at the field in England seeing him off on that last flight!" . It is now thought more than likely that Glenn Miller's plane was accidentally bombed by RAF bombers over The English Channel, after an abortive air raid on Germany and short on fuel dumping four thousand pounds of bombs in a safe drop zone to lighten the load. The logbooks of Royal Air Force pilot Fred Shaw record that a small mono engined plane was seen to spiral out of control and crash into the water.

Glenn Miller's music is familiar to many born long after his death, especially from its use in a number of movies. James Stewart starred as Miller in 1953's popular The Glenn Miller Story, which featured many songs from the Glenn Miller songbook, but which also took many liberties with his life story. For example, Marion Hutton, Paula Kelly, Tex Beneke and Ray Eberle are not mentioned at all.

Many of the Miller musicians went on to studio careers in Hollywood and New York after World War II. For example, Billy May, who became a much-coveted arranger and studio orchestra leader and backed up singers like Frank Sinatra, Rosemary Clooney, Anita O'Day, and Bing Crosby. Wilbur Schwartz[16], Herman "Trigger" Alpert, Johnny Best, and Ernie Caceres backed up many singers in the 1940s and 1950s. Coronetist Bobby Hackett soloed on "A String of Pearls" in 1941 with the Miller orchestra; his reputation only ascended in the years after.Hackett's "wistful trumpet solos added a unique and essential touch to music by everyone from Glenn Miller to Jackie Gleason to Dizzy Gillespie." Norman Leyden from the Army Air Force Band was a noted arranger in New York, who later composed arrangements for Sarah Vaughan, among other people. Johnny Desmond from the Army Air Force Band became a popular singer in the 1950s and starred on Broadway in the 1960s in "Funny Girl" with Barbra Streisand. [22] Kay Starr[23] became one of the most popular singers of the post-war period; she got her start with Glenn Miller in 1939 recording two sides, "Baby Me" and "Love With A Capitol 'You'".

The Miller estate authorized an official Glenn Miller "ghost band" in 1946. This band was led by Tex Beneke and had a make up similar to the Army Air Force Band: it had a large string section. "The orchestra's 'official' public debut was at the Capitol Theater on Broadway where it opened for a three week engagement on January 24, 1946. The theater held three or four thousand people, I guess-it was sheer bedlam, an incredibly exciting thing to hear, [said Bob Ripley]" Ripley also says, "People would call out from the audience 'where's Glenn?' and it was apparent that a lot of people didn't even know he wasn't with us."