Harris in the Spring (1937)

Band leader Phil Harris, through a misunderstanding, finds himself with a job as a professional escort, and a date to take a rich young society girl to a night club. She picks the club where the Harris band is playing. Phil is kept busy trying to keep the band from telling the girl who he really is, and to keep the girl distracted enough so she won't notice he is leading the band.

Unfortunately the movie Harris in the Spring is not yet available on HBO Max.