Top 5 Movies to Watch While Smoking a Cigar

Cigars and cinema go hand in hand. Cigar smoking has been immortalized in a number of blockbusters on the silver screen. Because smoking a cigar makes such a strong visual statement, a cigar is the ultimate prop in the hands of the right actor. Cigars communicate authority, brooding, and extravagance. The best directors know how to capture the smoking of a cigar with such seduction and artful enterprise it’s impossible not to crave one yourself. In fact, Alfred Hitchcock was regularly photographed smoking a cigar on the set of movies he directed.

When it’s your turn to host a movie night down in the man cave, we’ve put together a list of the 5 best movies to watch while you’re smoking cigars.

#1 - Darkest Hour (2017)

Let’s jump right in with the critically acclaimed film, Darkest Hour, featuring an Oscar-winning performance by Gary Oldman for his fastidious portrayal of Winston Churchill. In addition, the film scored Oscar wins for the team of makeup artists who diligently and meticulously transformed the actor into Churchill over the course of an hours-long process every day prior to shooting.

Not only is Darkest Hour a magnificent account of Churchill’s transition into the role of Prime Minister, Oldman also delivers a realistic and comprehensive depiction of Churchill’s iconic mannerisms, including his prolific cigar consumption. In an interview on “The Graham Norton Show,” the actor claimed he smoked roughly 12 cigars per day – approximately $30,000 worth of cigars – over the course of the film’s shooting schedule. Oldman consumed an abundance of Cuban Romeo y Julietas at a cost of nearly $60 per cigar.

Darkest Hour is a must-see for both World War II buffs and cigar lovers. The film’s many intense moments reveal a riveting account of the critical decisions confronting Churchill and Great Britain as Hitler set his sights on dominating the whole of Europe. The suspense is positively cigar-worthy. We suggest a smoking a prominent and rare blend like the 94-rated Ashton ESG while you’re glued to your seat.

#2 - Goodfellas (1990)

Sure, the wiseguys in Goodfellas smoked a lot of cigarettes. But, there are more than a few classic cigar-smoking scenes, too. The dapper Cadillac-driving gangsters who roll up to the cab stand in Henry Hill’s youth are met by cigar-smoking characters Tuddy Cicero and his brother, mob boss Paulie Cicero, who are rarely without cigars throughout the film.

Director Martin Scorsese’s entertaining and violent depiction of the New York mafia from the mid-1950s through the 1980s is now a classic in the pantheon of mob movies. At times brutal and comical, Goodfellas boasts as many famous scenes and unforgettable lines as any other film in the genre of crime drama you could compare it to.

The film’s era, unabridged narrative, and an all-star cast that includes Robert De Niro, Ray Liotta, Joe Pesci, Lorraine Bracco, Paul Sorvino, and Frank Vincent, among many other notables make Goodfellas an excellent flick to screen down in the man cave over cigars with your pals. Indulge in equally classic cigars like Arturo Fuente Hemingway.

#3 - Scarface (1983)

Al Pacino wields a cigar in an array of seminal cigar-smoking scenes as organically as he brandishes a gun in Oliver Stone’s 1983 American crime drama Scarface. A remake of a 1932 film inspired by Al Capone, Scarface chronicles the rise of main character Tony Montana from humble Cuban refugee to small-time criminal to a powerful drug lord.

The film’s prolific depiction of violence, profanity, and drug use earned it an initial rating of X from the Motion Picture Association of America (MPAA), preventing its screening in most theatres. Director Brian De Palma edited the film several times before finally getting a resubmitted version upgraded to a less restrictive R rating. Despite its polarizing reception and initial controversy, today Scarface is a cult classic and considered among the most successful works in its genre.

Firing up a premium cigar while you’re watching Scarface seems a fitting gesture to celebrate the film’s portrayal of power and excess. Consider a strong and spicy smoke like My Father Le Bijou 1922.

#4 - The Good, The Bad, and The Ugly (1967)

In a discussion of the best movies to watch while you’re smoking a cigar, it’s impossible to leave out a classic Western or two – or maybe a dozen. It’s most befitting we pay homage to none other than The Good, The Bad, and The Ugly, Sergio Leone’s crowning final installment in his Dollars Trilogy. The film is credited with launching Clint Eastwood into widespread stardom for his role as the Man with No Name.

A classic tale of buried treasure binds the film’s three principal characters in a quest to enrich themselves in the American Southwest during the Civil War era. Clint Eastwood as Blondie, a.k.a. the Man with No Name (The Good), Lee Van Cleef as Angel Eyes (The Bad), and Eli Wallach as Tuco (The Ugly), charter a treacherous course where their fates intertwine in an epic mission in a film long considered a benchmark by which all other Westerns are measured.

Eastwood’s performance is intrinsically linked with cigar smoking. Although the rugged-textured and basic taste of inexpensive Cheroots were chosen as Eastwood’s chief cigar prop, their coarse appearance mirrors the terrain of the film’s setting and underscores the actor’s now-iconic brooding nature. You don’t have to smoke a Cheroot necessarily, but The Good, The Bad, and The Ugly is always a joy to watch with a rich and spicy premium Nicaraguan cigar like San Cristobal Quintessence, a 95-rated classic awarded ‘#3 Cigar of the Year’ honors in 2021 by Cigar Aficionado.

#5 - The Godfather (1972)

The nearly inconceivable obstacles Francis Ford Coppola encountered from studio executives while filming The Godfather make us wonder how the movie ever got made. The making of The Godfather is nearly as riveting as the film itself as Coppola recounts in a revealing 2003 interview with Cigar Aficionado.

Today, The Godfather routinely appears at or near the top of lists of the greatest movies of all time. Relying heavily on his own familial experience as an Italian American, Coppola lent a tremendous sense of authenticity in his adaption of Mario Puzo’s bestselling novel. The epic narrative on the American mafia is easily among the most re-watchable films ever produced thanks to iconic performances from Marlon Brando, Al Pacino, Robert De Niro, James Caan, Robert Duvall, Diane Keaton, and many others.

While cigar smoking may not entertain a central presence onscreen, watching The Godfather calls for a supremely indulgent cigar like an Ashton VSG, Fuente Fuente Opus X, or a Padron Family Reserve. A Churchill or Double Corona size is best and you might consider getting a few because it’s almost impossible to take in The Godfather without immediately following it up with The Godfather II.