Sometimes, good things come in weird packages. While many cigars strive for a classic, ultra-traditional look and feel, others purposely break from convention — to excellent effect. With Halloween right around the corner, now’s the perfect time to review some of the strangest premium cigars you’re likely to see on the market. Here are a few cigar oddities to add to your collection:

Diesel Side Show

Diesel Side Show isn’t a single cigar but rather a limited-edition set of strikingly strange smokes. Not only are the names unusual (Frog Boy, Two-Headed Nightengale, for instance), but the cigars themselves are out of the ordinary — especially the Bohemian Twin Culebra — one of the rarest sights in the cigar biz. 

Drew Estate Undercrown Flying Pig

Drew Estate has a penchant for the uncommon. After all, they’ve released an egg-shaped cigar before. However, our favorite oddball Drew Estate smoke has to be the Undercrown Flying Pig. Sure, you can get Undercrown in more “normal” sizes, but there’s just something amusing about a squat, fat cigar that, well, looks like a pig.

Alec Bradley Filthy Hooligan

At one point, Candela wrappers enjoyed widespread popularity in the US market. Now, this green tobacco is rare, but the Alec Bradley Filthy Hooligan is an excellent barber pole that showcases a Candela wrapper alongside Nicaraguan Habano tobacco. Ideal for St. Patrick’s Day — or any day, really. 

La Flor Dominicana Chisel

La Flor Dominicana’s Chisel, which indeed has a wedge-like chisel shape, is a one-of-a-kind vitola in the cigar industry. While this cigar variety may seem odd at first, some versions of Chisel — notably the Double Ligero — have received exemplary ratings over the years. This is a smoke that turns heads for all the right reasons. 

Asylum April Fools’

If you want a humongous cigar that might not even fit in your humidor, look no further than the Asylum April Fools’ 9X90 (yes, you read that right). Asylum’s most eye-popping cigar will probably take you hours, if not days, to smoke, but what else would you expect from a cigar named after April Fool’s Day? 


What’s your favorite “weird” cigar? Let us know what you’re lighting up for Halloween, and sign up for Cigar World for more great content like this!

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