One of the strongest bonds in the spirits world defines the magic that happens when straight Bourbon meets a curling waft of cigar smoke. We paired two excellent cigars—a toasty, Padrón 1964 Anniversary Series Torpedo and a fuller-bodied Fuente Fuente OpusX Robusto—with 16 fine Bourbons. Our favorite with each whiskey is indicated by asterisks.
Angel's Envy Cask Strength (variable proof, tasted at 119.3, $169): Aged rum is the first impression with molasses, banana and graham cracker. Then comes Port, anise, cinnamon, cloves and cocoa.
- Padrón pairing: The whiskey overpowers the cigar a bit, but they make an accord through a like spice character.
- *Fuente pairing*: The Port finish explodes with this cigar, and the Bourbon returns graham cracker and other pleasant notes.
Bulleit Frontier Whiskey (90 proof, $27.99): This whiskey is a bit coy about its high-rye recipe, but exudes oak, vanilla and orange peel. Then comes fruit before spices like pepper, cinnamon and anise.
- *Padrón*: Bulleit draws sweet marzipan out of the cigar, while the Bourbon's rye spice is shown to better effect.
- Fuente: The whiskey's spice resounds and the Fuente becomes rounder. This is a close call.
Eagle Rare Aged 10 Years (90 proof, $29.99): Nose of caramel and vanilla with walnuts. The palate offers molasses, toffee and honey before taking on spice for an indelible finish.
- *Padrón*: The Bourbon accentuates the cigar's spice and toast, giving it creamy orange notes, while it shows its own vanilla.
- Fuente: A bit of a clash between sweet and earth flavors, but a sweet spot exists in the cigar's leather.
Elijah Craig 23 Aged Years Single Barrel (90 proof, $199.99): Not overly tannic, but creamy, with orange and berry notes as well as cinnamon and licorice.
- Padrón: A little too much whiskey for the cigar, but some pleasant connections.
- *Fuente*: A better balance of bodies allows the Bourbon's fruit to elicit a bonbon effect.
Four Roses Small Batch (90 proof, $39.99): A Bourbon that bespeaks its name with plenty of floral aspects as well as a spicy bite. A parade of hard candy fruits win the day.
- Padrón: The Bourbon's flowers pounce on this pairing, splashing candy on the cigar.
- *Fuente*: The cigar shows off its sweetness and the whiskey gets mellow.
Hillrock Solera Aged Bourbon (92.6 proof, $80): A nuanced Cognac nose, with caramel, vanilla, Sherry and spice on the palate.
- *Padrón*: The cigar's hearty notes fill out the Hillrock as the Padrón gets sweet and spicier.
- Fuente: The Hillrock is less ethereal and unmistakenly Bourbon-like, but without much payback.
Hudson Baby Bourbon (92 proof, $44.99, 375 ml): The pure-corn mash bill makes this whiskey sweet, with herbal, tannic and oily notes.
- *Padrón*: A sea change: the cigar smooths the edginess and finds a molasses character.
- Fuente: The same effect, but not as chewy.
Jefferson's Reserve Groth Reserve Cask Finish (90.2 proof, $79.99): Projects cinnamon and herbs with an underlying vanilla redolence. Wine notes transform into bigger berry flavors.
- *Padrón*: The cigar's toast lends a welcome bite to the Jefferson, and the two waltz around a shared spice.
- Fuente: The earthy cigar troubles this pairing, but the bourbon makes the smoke sweeter.
Jim Beam Signature Whole Rolled Oat (90 proof, $49.99 for 375 ml): Very sweet, fruit nose with spice and candy apple. Cherry, toffee, toast, nuts and tangerine on the palate.
- Padrón: A sublime balance of soft flavors. The whiskey is rounder and the cigar sweeter.
- *Fuente*: You completely forget the oat notion as you're lost in a swirl of caramel and licorice. Another tough choice.
Maker's Mark Cask Strength (variable proof, tasted at 113.2, $39.99): The high alcohol content never masks its citric flavor. Vanilla and maple candy are the second act, followed by cocoa and toffee.
- *Padrón*: Any heat on the Bourbon dissipates and the Maker's conjures orange peel in the cigar, which offers toast and marmalade.
- *Fuente*: Maple from the Bourbon transforms into a candy bar of chocolate and nuts. These are both winners.
Old Forester 1897 Bottled in Bond (100 Proof, $49.99): A huge nose of caramel and maple, with rye and a hint of candy.
- Padrón: Very well-balanced. The whiskey gets richer barrel flavors. The cigar gains maple and spice.
- *Fuente: These two find a hearty common ground, with leather and nuts, plus subtler notes like candy and spice.
Old Grand-Dad Bonded (100 proof, $24.99): High-rye recipe mashbill is the first to impress, but candied fruit and flowers fill in. Cinnamon tartness never overshadows the caramel/vanilla, banana, chocolate and cherry notes.
- *Padrón*: Tartness on the whiskey backs off to allow more caramel/vanilla. The cigar gets nuttier and creamier.
- Fuente: Candy resounds on the cigar. The whiskey is spicier.
Orphan Barrel Rhetoric (90 proof, $85): A floral nose, with leather. On the palate cinnamon, cherries and molasses chime in.
- Padrón: The cigar becomes heartier. The whiskey gets only tang in return.
- *Fuente*: This smoke's flavor range widens into fruits, cocoa and toast. Berry notes fade, but the spirit is heartier.
Wild Turkey Master's Keep (86.8 proof, $150): Not as woody as 17 years suggest. Complex, with grapes, toast, nuts, tea and light woods. Fruity on the palate.
- *Padrón*: Tea and toast are revived for a pretty pairing. There's a synergy of sublime spice.
- Fuente: Not as successful. The cigar trades in earth and leather for some fruit.
Woodford Reserve Double Oaked (90.4 proof, $49.99): Beyond the oak, caramel and toffee is a dose of spice including clove.
- Padrón: The clove disappears as the whiskey dries a bit, but the cigar gains a toffee note.
- *Fuente*: The whiskey's spice is kickstarted as the Fuente becomes subtler and gains some pepper and sweetness.
Wyoming Whiskey (88 proof, $43): A floral nose with some fruit and vanilla. Wheat, fruit and herbs on the palate.
- *Padrón*: The cigar makes the whiskey softer and nuanced.
- Fuente: Played well. The whiskey injected sweetness in the cigar.