What Is a Cheroot Cigar?

A cheroot is a small, rough-looking machine-made cigar. Cheroot isn’t a term we hear regularly today. It sounds like something out of the Wild West – but that’s largely because we associate cheroots with cowboys thanks to Clint Eastwood’s portrayal of The Man with No Name in Sergio Leone’s famous Spaghetti Westerns. Cheroots originated in India and gained popularity among the British during the peak of the British Empire. Cheroot is derived from the Tamil word curuțțu, which means roll in the dialect of South Asia’s Tamil culture. Cheroots are often lumped in with cigarillos, another small-format machine-made cigar, but there are subtle distinctions between the two.

What’s the Difference Between a Cheroot vs. a Cigarillo?

Cheroots resemble twigs. They’re open on both ends, around 3 to 4 inches long with a slender ring gauge, and some of them taper. Their rugged and rough texture is a novelty for cigar lovers, but it also contributes to their popularity. You can buy cheroots in gas stations and convenience stores as well as cigar shops. Their taste can be as hash as their appearance, depending on the brand. Some manufactures like Backwoods and Avanti produce flavored cheroots to disguise the naturally bitter taste of the tobacco.

Cigarillos exhibit a smoother, more uniform look. They’re also 3 to 4 inches long with ring gauges between 20 and 30. Cigarillos are crafted from the leftover tobacco that goes into premium handmade cigars. They’re popular for their mild, nutty, and elegant flavor. Most premium brands manufacture cigarillos for cigar lovers who don’t have time to smoke a traditional handcrafted size. Cigarillos are generally sold in premium cigar shops.

Neither cheroots nor cigarillos are meant to be inhaled when you’re smoking. Draw the smoke into your palate and expel it like you’re smoking a traditional handmade cigar. If one end of a cheroot or a cigarillo is tapered, that’s the end that goes in your mouth.

What Kind of Cigars Did Clint Eastwood Smoke?

In Sergio Leone’s iconic Dollars Trilogy, the Spaghetti Western genre was established with Clint Eastwood’s portrayal as the poncho-wearing, revolver-wielding, and cigar-smoking Man with No Name. His seriousness and uncompromising pursuit of justice resonate with audiences today.  A Fistful of Dollars (1964), For a Few Dollars More (1965), and The Good, the Bad, and the Ugly (1966) are regarded as quintessential Westerns – and cigar smoking is critical to the cinematography.

Although the Man with No Name is a protagonist, the cigars he chomps on add a dark aura to his character. Many assume Eastwood smoked De Nobli Toscani cigars, due to Leone’s Italian heritage, but it’s likely he smoked an American brand called Virginians according to the James J. Fox Cigar Shop in London. Leone insisted the Man with No Name smoke to reflect the character’s mystique.

What are the Best Cheroots?

Ranking the best cheroots to smoke is like ranking the best spam. Cheroots aren’t the most romantic cigars by any standards, but they enjoy a niche audience. Popular brands include Kentucky Cheroots, Red Lion, De Nobli Toscani, Ugly Coyote, and Henry Clay. Honey, bourbon, berry, and anise-flavored cheroots are available from brands like Avanti and Backwoods. Some guys simply smoke cheroots to look tough like Clint Eastwood, which is more believable than appreciating the flavor.