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According to an interview in 1919, Walter Hiers said his first appearance was as a bell-hop in SAVED FROM HIMSELF (Biograph 1911 directed by you-know-who) with Mabel Normand. It is not listed in his filmography, nor in the credits of "DW Griffith and the Biograph Company". I just watched i...

...and of course Milburn Morante.

Jack comes on around the 18 minute mark and Mel joins him around the 40 minute mark for about 10 minutes. Funny and heart-warming.

https://www.youtube.com/watch?v=Pw7rIQrO5II&t=4107s

And Charles Dorety channeling Buster Keaton in Third Class Male (Century Comedies 1921 directed by William Watson)

https://www.youtube.com/watch?v=pRm_vC9mu-c

Here's an endearing 1992 bio "Jack Benny Comedy in Bloom", narrated by Tom Smothers. The talking heads all worked with him and the affection they felt for him feels very genuine.

https://www.youtube.com/watch?v=0b51SKLTZNY

I was asked about this one, but out of my depth. Perhaps Al Alt?

https://www.youtube.com/watch?v=-K3mNNhPGKc

IMPORTANT NEWS (MGM 1936) with Chic Sale, James Stewart and everybody's favorite, Billy Dooley

https://www.youtube.com/watch?v=YTLkU9CKvKY

Patsy Kelly in possibly her first film:

https://www.youtube.com/watch?v=gfAqC-WXuwE&t=338s

Jay C. Flippen is mostly remembered as a stellar character actor from the late 1940's through 1970, but he was in vaudeville from the early 1920's and had a unique style. Here is THE HAM WHAT AM, a Vitaphone Variety from 1928:

https://www.youtube.com/watch?v=I68kv3UNWuM

A product of it's time, apparently Freeman & Gosden do the voices here as well

https://archive.org/details/amosnandyrasslingmatch