I had some tolerance for detective shows (Sam Spade) or movie adaptations (Lux Radio Theater), but the one genre I wouldn't touch was comedy. To me, nothing in old-time radio seemed more dated than the comedy shows; many of them even grated on me*.
I would make an exception on certain occasions. In December, the days leading up to Christmas Eve would feature Christmas-themed shows and I would even listen to the comedy shows then. And every October 31st there would be a Halloween-themed lineup. Each year I would make a point of sitting up to listen, hoping for some show I hadn't heard before (the Weird Circle episode "Curse of the Mantel" was one I first heard on a Halloween), or at least the Mercury Theater's War of the Worlds adaptation (although having heard it dozens of times since then, it's lost a little potency for me).
And so, one Halloween I heard an episode of the Jack Benny Program. I don't think I had ever sat through a full episode before, but I considered it worthwhile just to get to the horror shows coming up afterward. The episode (from November 2, 1947) opened with some Halloween-flavored jokes, then went into a sketch where the cast parodied the Humphrey Bogart film Dark Passage.
"Why do they always have such good singers in prisons?"
At the time, I hadn't seen Dark Passage. I considered myself distinguished just for knowing Bogart. This did not matter. There were no real jokes about the film, as the sketch was mostly prison jokes (in the film, Bogart springs prison in the opening scene) and then plastic surgery jokes (which is what Bogart does in the next sequence). There weren't even jokes specifically about Bogart. Complete ignorance of the film had no impact on the sketch's effectiveness, which is certainly a statement when you consider how much of modern comedy relies on unusual pop culture references.
The part of the sketch which won me over to Jack Benny was this:
BENNY: "The guard took me to the warden. I'll never forget that harrowing walk down the long, long corridor. As I passed the condemned cells, the guard said:"
GUARD: "Poor devils; they're doomed."
BENNY: "As I passed the solitary cells, the guard said:"
GUARD: "Poor devils; they'll go crazy."
BENNY: "As I passed the women's cells, the guard said:"
BENNY: "As I passed the work cells, I stopped and went back for the guard."
And so, my resistance against old-time radio comedy was broken. For a long time, Jack Benny was the only program I made a point of listening to, but I learned to enjoy other programs of the day like Life of Riley, the Stan Freberg Show and Burns and Allen. I owe it all to having listened to that one episode of Jack Benny. You can hear it here.
(* and many still do; I can only take so much of high-pitched or squeaky voices used on shows like Father Knows Best, Aldrich Family or Portland on Fred Allen. And Lucille Ball? Only in small doses.)