Far be it from us to endorse and advocate the deadly habit of tobacco smoking, but also far be it from me to whitewash history. When I was a kid, “old Jewish comedians with cigars” was a thing, and they were all veterans of vaudeville or the Borscht Belt. Traditionally, it wasn’t solely a Jewish thing, as you’ll see on the list below, it’s just that the handful who lived to be old enough for me to see them on TV tended to be of that culture. With the exception of Bill Cosby, the younger comedians of my time tended not to smoke them, they were very much out of fashion and associated with “the Establishment”. Fogeys with stogies! (I’ll always have a fond memory of going to into a credit union with my dad as a small child in the early ’70s, and my dad introducing me the cigar smoking bank manager, a man named Mr. St. Germain. He seemed like an important guy, but also some kind of holdover from another era).
The hey day of cigars in show biz was the 1920s through the ’50s, and that’s not coincidental. Good cigars are expensive, and strictly a luxury item. Think about it: it’s something you burn and throw away. It is the ultimate emblem of Thorstein Veblen’s “conspicuous consumption”. For vaudeville performers, cigars were of a piece with expensive jewelry and a high-end wardrobe. It was there to project prosperity, stability, optimism, and confidence. It reassured everyone who needed to be reassured that America was a great country, and that we were are all going places together. And yet, because it was a vice, it wasn’t elitist either. It was kind of levelling. It declared that in this foible, the entertainer had a weakness, just like you.
For a comedian, obviously a cigar is not just a handy drug delivery system, or an amusing prop. It’s a wonderful, organic assist to comic timing. You smoke during the laugh — it looks better than just standing there waiting for the laughter to subside. For stand-ups, it’s also a wonderful visual, the only horizontal working against the vertical impression created by the comic and his mike stand.
In the early days, cigars were among the many things banned from vaudeville (like swearing, boozing, and sexual innuendo). Vaudeville was originally defined by its “purity”. Cigars were part and parcel of the saloon variety that had preceded it. Ironically, Oscar Hammerstein, one of the greatest of the early vaudeville moguls had literally built his fortune on the manufacture of cigars! By vaudeville’s last decade, the 1920s, prudery (on that level at any rate) was waived within reason to accommodate big stars.
Anyway, here are a handful of the top entertainers who kicked a significant portion of their salaries over to cigar stores.
Obviously! Groucho had taken up the habit as a teenager, no doubt with stars in his eyes, as he was wanting to break into vaudeville. So much is he associated with cigars that lame impressions of him always depict him holding one.
Burns’ association with the cigar is tied primarily to his last few decades, from the time of the Burn and Allen tv show onward. In the ’80s and ’90s he joked that smoking was the only thing keeping him alive.
It wasn’t a trademark for Berle like it was for Burns and Groucho, but one usually saw Berle with a cigar in his puss during his later decades. Ironic, eh? For there was a guy who required no Freudian assist,
As Benny’s biggest stardom was on radio, only his live audiences saw him with a cigar, though he shared the habit with his peers. Towards the end of his life, he told an anecdote on The Tonight Show with Johnny Carson about driving in his car, realizing that the cigar tasted terrible, so he threw it out the window. And that was apparently how he quit smoking, although he quipped that his parsimonious nature had him wanting to drive back to retrieve it.
Chronologically, Jessel may rate being placed first on this list, though he’s somewhat forgotten today. He hasn’t left an imprint on popular memory as big as some of the others. I think of Jessel as being the most disgusting of the cigar smoking comedians, all chewing on the end and getting the thing soaked in spit. (Late Berle was like that, too). Blecch!
Frisco’s comedy was largely offstage, he was prized for his legendary quips. But he also starred in the amazing comedy short The Happy Hottentots (1930). He’s celebrated mostly for bringing cigar smoking into dancing. He used the cigar and the smoke it generated in his dance act, surely providing the inspiration to Bob Fosse to later do the same.
Invariably with a cigar in his puss, Clark (of the team of Clark and McCullough) would charge around the stage like a scene-chewing dynamo, devouring anything and everything in his path. A favorite trick of his was to spit his cigar out and catch it a couple of feet in front of his face, then continue smoking.
Today, Bob Woolsey, of the team of Wheeler and Woolsey, reads to new audiences like a sort of cross between Groucho and George Burns. As a movie star of the ’30s though his public association with the cigar pre-dates Burns’s by many years, and I’ve long suspected that some of the later guys emulated Woolsey.
Penner, of course, was associated with his pet duck above all things, but he usually had a cheroot in his kisser.
Murray claimed to have been the first stand-up comedian to make smoking a cigar a part of his act, on account of being the youngest big time comic (he was in his early twenties) and wanting to add some “experience” to his persona. His claim is plausible. With the exception of Groucho, who smoked in an act with his brothers and a bunch of other people, I can’t think of anyone else smoking cigars on stage prior to Murray. Initially, it had been part of their offstage behavior. Then at some point, maybe after Murray tried it, it became a thing on stage.
No one is more associated with cigars than Ernie Kovacs; I’ve only put him this far down on the list because he was from a younger generation. Not only can I not even picture Kovacs without a cigar, Dutch Masters sponsored his show.
A new generation, very much in the tradition of the old. I think of Jack Carter and Jan Murray with cigars too but couldn’t find any pictures.
His remake of The Jazz Singer notwithstanding, Thomas was not a Jew but a Lebanese Christian. But you must admit that “old Jewish comedians — and also a Lebanese Christian — who smoke cigars” doesn’t roll off the tongue like cigar spit.
Naturally there were other cigar smoking comedians beyond these ones before, during, and after vaudeville. Contemporary ones are most assuredly doing so in emulation of these older guys and their cohorts though. Cigars, along with capitalism, came back in fashion in the ’80s, though it remains at the fringes, a sort of forbidden pleasure, trotted out at the end of a night on the town, or on special occasions. I’ve often toyed with the idea of reviving it as an onstage thing, but it happens to be against the law most places. Ron White, how do you do that? Do you just pay the fines?
For more on vaudeville and old school comedy, please see No Applause, Just Throw Money: The Book That Made Vaudeville Famous,
(Travalanche) 
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