The 10 funniest people in old-time radio

Dennis Day

10.  Dennis Day (The Jack Benny Show, A Day in the Life of Dennis Day)
Hired as a singer by Jack Benny (on a nudge from wife Mary Livingstone) Dennis Day burst upon the radio scene after having been a Mouseketeer in the radio version of The Mickey Mouse Club.

Yes, Dennis could sing with the best of them and made dozens and dozens of record albums using his tenor voice. But most radio fans know him as the simpleton who was a master of dialects and mimics.

 9.  Harold Peary (Fibber McGee and Molly, The Great Gildersleeve)
Blessed with a booming voice and a laugh that will go down in the annals of recorded history, Peary became so popular as the fourth or fifth fiddle on Fibber McGee and Molly that he became the first person in the history of radio or televison to get a "spin-off" - his own show based on a character he created on another show.

Moving to The Great Gildersleeve set, Peary was funny enough but was very fortunate to be surrounded by a wonderful cast that included Walter Tetley, Lurene Tuttle, Earle Ross, Arthur Q. Bryan and Shirley Mitchell (among others.)

His interaction with "nephew" Leroy is some of the best radio you'll ever hear.

Red Skelton

 8.  Red Skelton (Rudy Vallee Show, The Avalon Program, The Red Skelton Show)
Skelton was a clown who made waves on radio due to the fact that he had several different characters he could become at the drop of the hat.

Some of his more popular characters included Mean Wittle Kid, Willy Lump Lump and Clem Kadiddlehopper (among many others.)

 7.  Gale Gordon (Fibber McGee and Molly, Phil Harris-Alice Faye Show, Our Miss Brooks)

Gale Gordon

Gale Gordon was a great actor and his penchant for having a fine, booming voice made him a great character actor as well (often playing a mean boss-type.)

He was one of the most used actors in radio and I think his finest character ever was Mayor LaTrivia on Fibber McGee and Molly.

Fibber liked to mix up LaTrivia and Gordon's babble in rebuttle is hilarious stuff.

 6.  Milton Berle (Rudy Vallee, The Milton Berle Show)
A one-man, machine gun-like joke machine who could ad-lib with the best of them. He could also sing, write music and though I am not sure about this: could probably dance as well. Enormously talented, he was more funny than anything else.

His height of popularity came in the early 1950's though as he left radio and became known as, "Mr. Television."

 5.  Fanny Brice (Ziegfeld Follies of the Air, many shows with various names)
Fanny Brice became a giant hit when she turned into Baby Snooks, a large child we "saw" as being crane-like, with giant limbs and an ugly face. Her routine was destroying the peace and quiet her daddy craved and making life miserable for him.

She was loud and curious and gullable and sly - and Brice took each of these abilities and created a giant baby monster, with hilarious results.

 4.  Jim Jordan (Fibber McGee and Molly)
A master of puns and tricky speech elocution, quick words and tall tales, Jordan was the sun that the Fibber McGee and Molly show revolved around.

The entire show was good with it's superb cast and great writing - but Jordan took the McGee character and let him run wild, so much so that we don't really know what the real Jim Jordan was really like.

Bill Thompson in a Fibber Mcgee & Molly film

 3.  Bill Thompson (The Breakfast Club, Fibber McGee and Molly)
Thompson played various characters who met up with Fibber McGee and Molly.

My favorite was always the Old Timer but he could turn around and play the meek and mellow Mr. Wimple (and many other characters as well.)

No matter who he was, he was funny.

 2.  Arnold Stang (The Milton Berle Show)
Four eyed Stang looked harmless enough but was as brash and loud as anyone could be often touting ridiculous threats with surprising conviction, all in Brooklyneese.

Stang was funny because he was someone who was not as he looked - therefore, Stang was a fine actor with his voice and went on to do loads of cartoons in the tv era.

TIE
 1.  Walter Tetley (The Great Gildersleeve, Phil Harris-Alice Faye Show)
Like Stang, another harmless-looking fellow with a wise guy Brooklyn accent, looking for trouble and often finding it, often with hilarious results.

His voice made him lots of money in the tv era as well.

 1.  Groucho Marx (mostly You Bet Your Life)
Ballsy comedian with crazy looks and an outspoken personality (he too with a Brooklyn accent) was really very talented in a lot of areas. But the thing that sticks out was his humor; no one was faster with a comeback (always a funny one) and he had the power (and often used it) to make people look foolish.

As heartless as he seemed, he was still the funniest person in the world - or at least tied with Walter Tetley, who like Stang before him on the list - are both similar to Groucho.