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The Horn Blows at Midnight (1945)
A Comedy Classic
If you have to watch one Jack Benny movie, this one would probably be the one to watch. As other reviewers have noted, this movie bombed at the box office after its release and Benny joked about this fact often in his monologues. Even though it was poorly received at the time it came out, its stands up better now. Its best when watched not just as a comedy but as a parable that has timeless themes, that are not just relevant to the 1940's.
Good versus evil, greed versus generosity, heaven versus life on earth. The "fish out of water" sequences where Jack Benny, as an angel, struggles to adjust to the realities of life on earth, are also very funny and timeless. All that and Jack Benny's warm and funny screen presence make this an appealing picture.