Fred Allen, February 22, 1939
Fred Allen has at least two appearances (via reference) in cartoons in 1939; as Krazy Kat's voice in Krazy's Bear Tail and being imitated by the Edward G. Robinson character in Thugs with Dirty Mugs.
Note the theme song is cartoon related song Smile Darn Ya Smile (in keeping with sponsor Ipana Toothpaste). More cartoon music about 15 minutes in as well (Raymond Scott's The Toy Trumpet). Allen's show would also eventually have Senator Claghorn in the '40s, the supposed source for Foghorn Leghorn's voice.
The show is, to my ear, a cluttered mess. The Benny program is half the length and ten times as structured. I don't understand how the Allen show was as big as it was; the material isn't bad line to line, but it's all over the place. It is clear to me why Benny is still an echo in culture while Allen is more or less a footnote to that echo. It doesn't help Allen's legacy that he died in the '50s, or that he reportedly hated television in some manner (a manner which didn't keep him from being a panelist on What's My Line for two years) of course, but I think it is deeper than that.