The August 31st, 1980 archive show

[R H Draney]

In the introduction to the #2 song on the countdown for the recently
archived show #80-35, Dr Demento mentioned that as far as he could tell,
"That Baseball Rag" by Arthur Collins was the oldest recording ever to make
the Funny Five....

Did anyone ever do the research to confirm whether this was true at the
time, and whether it was or not, has the record been broken since then?...r

[Jeff Morris]

Strictly speaking, I think it was true at the time. I haven't checked every single item ever to "chart" on the show, but there are very few artists he's played on any regular basis that recorded prior to 1913, and which could've had a chance at the Funny Five.

But, for a counterexample of sorts, we see that "No News" by Nat M. Wills (from 1908) hit #5 on the top five in summer 1972, possibly July 23. But this was before syndication, thus not likely to count in such a statistic announced on the syndicated show, and also it was termed the "top five" at that point, not the "funny five", so strictly speaking this isn't a counterexample.

As for the record being surpassed on a later episode, here's another counterexample that really isn't. On 84-25, he played "Great-Grandad's Funny Five" and included "Uncle Josh Buys An Automobile" at #5. First of all, this isn't the real weekly Funny Five from that show, and also without checking I don't know which recording of that he played. Cal Stewart recorded many of his bits multiple times.

So I'd say this record stands, for syndicated Funny Fives. But if someone has a real counterexample, enlighten us! :)