I first encountered Jack Benny when black & white television came to Oz, but he wasn't much to my taste back then. But when audio downloads came into fashion maybe 20 years ago, I came across him again and he grew on me. It's dated of course, I mean some of this stuff goes back to the 1940s, but the tricks of the comedy trade haven't changed a lot even if the subject matter has. It mainly comes down to timing and having good writers, and Benny has both. And repetition of situations is another thing. Seinfeld has a lot of that, all the good comedians do.
Hope you enjoy some of it. ps I'd skip the real early ones, the sound quality is not so good.